Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

ABSTRACT

Transition metal (TM)‐catalyzed photoreactions have emerged as powerful tools for synthesizing products that are challenging to obtain under conventional thermal conditions. However, most protocols rely on short‐wavelength visible light, such as purple or blue light (<500 nm). Although long‐wavelength light (>500 nm) allows for milder conditions, higher chemical selectivity, and deep light penetration, its application in single TM‐catalyzed photocatalytic systems is rare. Herein, we present the long‐wavelength visible‐light‐accelerated Rh(III)‐catalyzed olefination of arenes bearing an anilide moiety as a directing group. This methodology circumvents the use of external photosensitizers and short‐wavelength blue light, owing to the use of a cationic Rh(III) complex. Experimental and computational analyses suggest that the Rh(III) complex initially acts as a C─H activation catalyst, and oxidation of the generated Rh(III) hydride intermediate by oxygen is accelerated by absorption of long‐wavelength visible light (> 500 nm).

DOI： 10.1002/chem.202503055

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.5c03986

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.5c03987

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.5c03734

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jacsau.5c00831

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.5c01903

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

Basic 1,3-azole-directed C(sp³)–H borylation is challenging due to potential catalyst deactivation and the CN bond reduction with pinacolborane (HBpin) generated during borylation with B₂(pin)₂.

DOI： 10.1039/d5cc03115j

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

Azulene derivatives have attracted much attention for their application in organic electronic materials and devices because of their large dipole moment and small HOMO–LUMO energy gap. As these physical properties of azulene depend on its substitution and condensation patterns, developing methods to synthesize functionalized and π‐extended azulenes is desirable. However, synthesizing π‐extended azulenes requires harsh reaction conditions, making it hard to achieve both functionalization and π‐extension. Here, we report the synthesis of electron‐deficient azulene‐embedded polycyclic aromatic hydrocarbons (PAHs) with two alkoxycarbonyl groups by the rhodium‐catalyzed intermolecular arylative [2 + 2 + 1] annulation of teraryl diynes with dialkyl acetylenedicarboxylates followed by oxidation at room temperature. Interestingly, for the electron‐rich diyne, prolonged oxidation time after the arylative [2 + 2 + 1] annulation yields a helicene‐like bis(azulene‐embedded PAH) in good yield. Thus, obtained electron‐deficient fused azulenes have small HOMO–LUMO energy gaps (up to E _g ^elec  = 1.52 and E _g ^theo  = 2.06), resulting in long‐wavelength absorption extending into the near‐infrared region. Due to bulky electron‐withdrawing groups and π‐extension, the molecule becomes saddle‐shaped and highly polarized, and strong π–π stacking interactions are observed in both the solid and solution states.

DOI： 10.1002/anie.202505622

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.4c07249

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.joc.4c01693

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/s44160-024-00604-7

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Other Link： https://www.nature.com/articles/s44160-024-00604-7

Publishing type：Research paper (scientific journal)   Publisher：Wiley  

We have developed the Rh‐catalyzed enantioselective [2+2+2] cycloaddition of homopropargyl enamides (tosylamide‐tethered 1,6‐enynes) with alkynes to construct tetrahydroindole skeletons found in natural alkaloids and pharmaceuticals. This cycloaddition proceeds at room temperature in high yields and regio‐ and enantioselectivity with a broad substrate scope. The preparative scale reaction followed by substituent conversion on the nitrogen atom and the diastereoselective [4+2] cycloaddition with singlet O2 affords hexahydroindole‐diols bearing three stereogenic centers and variable substituents on the nitrogen. Mechanistic studies have revealed that the substituents of the enynes change the ratio of intramolecular and intermolecular rhodacycle formation when using terminal alkynes, varying the ee values of the cycloadducts.

DOI： 10.1002/anie.202404310

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

We have developed the Rh‐catalyzed enantioselective [2+2+2] cycloaddition of homopropargyl enamides (tosylamide‐tethered 1,6‐enynes) with alkynes to construct tetrahydroindole skeletons found in natural alkaloids and pharmaceuticals. This cycloaddition proceeds at room temperature in high yields and regio‐ and enantioselectivity with a broad substrate scope. The preparative scale reaction followed by substituent conversion on the nitrogen atom and the diastereoselective [4+2] cycloaddition with singlet O2 affords hexahydroindole‐diols bearing three stereogenic centers and variable substituents on the nitrogen. Mechanistic studies have revealed that the substituents of the enynes change the ratio of intramolecular and intermolecular rhodacycle formation when using terminal alkynes, varying the ee values of the cycloadducts.

DOI： 10.1002/ange.202404310

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

Abstract

Photolysis is an attractive method in organic synthesis to produce free radicals through direct bond cleavage. However, in this method, specific irradiation wavelengths of light have been considered indispensable for excitation through S₀–S_n or S₀–T_n transitions. Here we report the photoinduced homolysis of electronegative interelement bonds using light at wavelengths much longer than theoretically and spectroscopically predicted for the S₀–S_n or S₀–T_n transitions. This long-wavelength photolysis proceeds in N–Cl, N–F, and O–Cl bonds at room temperature under blue, green, and red LED irradiation, initiating diverse radical reactions. Through experimental, spectroscopic, and computational studies, we propose that this “hidden” absorption is accessible via electronic excitations from naturally occurring vibrationally excited ground states to unbonded excited states and is due to the electron-pair repulsion between electronegative atoms.

DOI： 10.1038/s42004-024-01208-0

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Other Link： https://www.nature.com/articles/s42004-024-01208-0

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Dearomative construction of multiply‐fused 2D/3D frameworks, composed of aromatic two‐dimensional (2D) rings and saturated three‐dimensional (3D) rings, from readily available quinolines has greatly contributed to drug discovery. However, dearomative cycloadditions of quinolines in the presence of photocatalysts usually afford 5,6,7,8‐tetrahydroquinoline (THQ)‐based polycycles, and dearomative access to 1,2,3,4‐THQ‐based structures remains limited. Herein, we present a chemo‐, regio‐, diastereo‐, and enantioselective dearomative transformation of quinolines into 1,2,3,4‐THQ‐based 6‐6‐4‐membered rings without any catalyst, through a combination of nucleophilic addition and borate‐mediated [2+2] photocycloaddition. Detailed mechanistic studies revealed that the photoexcited borate complex, generated from quinoline, organolithium, and HB(pin), accelerates the cycloaddition and suppresses the rearomatization that usually occurs in conventional photocycloaddition. Based on our mechanistic analysis, we also developed further photoinduced cycloadditions affording other types of 2D/3D frameworks from isoquinoline and phenanthrene.

DOI： 10.1002/anie.202403461

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/s44160-024-00527-3

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Other Link： https://www.nature.com/articles/s44160-024-00527-3

Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.4c00572

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.4c00268

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Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

DOI： 10.5059/yukigoseikyokaishi.81.930

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20230105

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.202304041

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.3c00895

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/s44160-023-00318-2

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Language：English   Publishing type：Research paper (scientific journal)  

The synthesis, characterization, and catalytic performance of an iridium(III) catalyst with an electron-deficient cyclopentadienyl ligand ([CpEIrI2]2) are reported. The [CpEIrI2]2 catalyst was synthesized by complexation of a precursor of the CpE ligand with [Ir(cod)OAc]2, followed by oxidation, desilylation, and removal of the COD ligand. The electron-deficient [CpEIrI2]2 catalyst enabled C-H amidation reactions assisted by a weakly coordinating ether directing group. Experimental mechanistic studies and DFT calculations suggested that the high catalytic performance of [CpEIrI2]2 is due to its electron-deficient nature, which accelerates both C-H activation and Ir(V)-nitrenoid formation.

DOI： 10.1002/anie.202301259

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.202301346

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

Base-mediated intermolecular macrocyclization and Rh- or Ni-catalyzed intramolecular double [2 + 2 + 2] cycloadditions allow enantio- and diastereoselective synthesis of planar chiral [2.2]triphenylenophanes.

DOI： 10.1039/d3sc00571b

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Language：English   Publishing type：Research paper (scientific journal)  

Transition metal photo-induced catalysts operating in a single catalytic cycle are preferable compared with binary catalytic systems comprising both transition metal and photoredox catalysts. Such single-catalyst systems perform the dual function of visible light absorption and chemical transformation. However, most visible-light-driven catalytic reactions proceed via radical mechanisms, limiting the reaction types to which the catalysts are applicable. Several non-radical catalytic reactions have been developed, but these reactions are substrate dependent owing to the low visible-light-harvesting ability of the catalysts. Here we report the design, synthesis and visible-light-induced non-radical reactions of dual-functional Rh catalysts, spiro-fluorene-indenoindenyl (SFI)-Rh(I) complexes. The SFI-Rh(I) complexes with non-fused but π-extended ligands reduce substrate dependence owing to high visible-light-harvesting ability, and show high stability due to resistance against protonation. Thus, the SFI-Rh(I) catalysts extend the scope of typical Rh(I)-catalysed reactions, such as the C–H borylation of arenes and [2+2+2] cycloaddition of alkynes, to challenging substrates under blue light-emitting diode irradiation at room temperature.

DOI： 10.1038/s44160-023-00268-9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

Abstract

Organoboron and organosilicon compounds are used not only as synthetic building blocks but also as functional materials and pharmaceuticals, and compounds with multiple boryl and silyl groups are beginning to be used for these purposes. Especially in drug discovery, methodology providing easy stereoselective access to aliphatic nitrogen heterocycles bearing multiple boryl or silyl groups from readily available aromatic nitrogen heterocycles would be attractive. However, such transformations remain challenging, and available reactions have been mostly limited to dearomative hydroboration or hydrosilylation reactions. Here, we report the dearomative triple elementalization (carbo-sila-boration) of quinolines via the addition of organolithium followed by photo-boosted silaboration, affording the desired products with complete chemo-, regio-, and stereoselectivity. The reaction proceeds via the formation of silyl radicals instead of silyl anions. We also present preliminary studies to illustrate the potential of silaboration products as synthetic platforms.

DOI： 10.1038/s41467-023-36161-4

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.2c05683

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Trivalent group-9 metal catalysts with a cyclopentadienyl-type ligand (CpMIII; M = Co, Rh, Ir, Cp = cyclopentadienyl) have been widely used for directed C-H functionalizations, albeit that their application to challenging C(sp3)-H functionalizations suffers from the limitations of the available directing groups. In this report, we describe directed C(sp3)-H amidation reactions of simple amide substrates with a variety of substituents. The combination of an electron-deficient CpERh catalyst (CpE = 1,3-bis(ethoxycarbonyl)-substituted Cp) and an electron-deficient 2-pyridone ligand is essential for high reactivity.

DOI： 10.1002/anie.202213659

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

Helicenes have excellent chiroptical properties derived from their helical chirality and so attract the attention of scientists for their potential application to chiral organic functional materials. Thus, developing an enantioselective synthetic method for helicenes is an important goal in organic synthesis. Here we describe the enantioselective synthesis of helicene and helicene-like molecules by cationic rhodium(I)/bisphosphine complex-catalyzed [2+2+2] cycloaddition reactions. The enantioselective intramolecular [2+2+2] cycloaddition reactions of 2-naphthol-linked triynes afford [7]helicene-like molecules in good yields and ee. [9]Helicene-like molecules and fully aromatic carbo[7]helicenes can also be synthesized enantioselectively by intramolecular [2+2+2] cycloaddition reactions. The enantioselective sequential intramolecular [2+2+2] cycloaddition reactions of variously linked hexaynes afford either a [11]helicene-like molecule or an S-shaped double helicene-like molecule, both in high ee. Cationic rhodium(I)/biaryl bisphosphine complexes can catalyze not only intramolecular reactions, but also intermolecular ones between tetraynes and 1,4-diynes to afford [7]-[9]helicene and helicene-like molecules. We also describe some representative examples of the enantioselective synthesis of helicene and helicene-like molecules by [2+2+2] cycloaddition reactions using transition metal catalysts other than rhodium (iridium, nickel, and palladium).

DOI： 10.5059/yukigoseikyokaishi.80.1019

CiNii Books

CiNii Research

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Other Link： https://ndlsearch.ndl.go.jp/books/R000000004-I032517197

Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.2c04740

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.joc.2c01885

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ejoc.202200690

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.202202542

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/s44160-022-00043-2

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Other Link： https://www.nature.com/articles/s44160-022-00043-2

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Angewandte Chemie International Edition  

DOI： 10.1002/anie.202200800

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.202200064

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

The Cp^E Rh(<sc>iii</sc>) complex enabled the catalytic oxidative annulation of 1-naphthols with internal alkynes under mild conditions. This catalyst lowers the activation energies for the concerted metalation-deprotonation and the reductive elimination.

DOI： 10.1039/d1ob02181h

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Language：Japanese   Publishing type：Research paper (conference, symposium, etc.)  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

A rhodium(III) complex bearing a 1,3-bis(ethoxycarbonyl)-substituted or an unsubstituted cyclopentadienyl ligand (CpE or Cp) significantly accelerates a variety of oxidative C–H bond functionalization reactions. However, the driving force of the acceleration compared with a conventionally used Cp*Rh(III) complex has not been elucidated. Herein, we performed density functional theory (DFT) calculations of the rhodium(III)-catalyzed oxidative C–H bond olefination and annulation reactions using Cp*, Cp, and CpE ligands, which revealed that the CpERh(III) complex stabilizes transition states of not only a C–H bond activation step but also rate-determining reductive elimination and insertion steps by strong orbital interactions. For the sterically demanding substrates, the less sterically hindered CpRh(III) complex can stabilize the transition states of the reductive elimination step more than the CpERh(III) complex. Moreover, the whole reaction pathways were calculated to elucidate the mechanism and selectivity of the oxidative [4 + 2] and [2 + 2 + 2] annulation reactions under cationic and neutral conditions, respectively.

DOI： 10.1021/acscatal.1c03454

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Language：Japanese   Publishing type：Research paper (conference, symposium, etc.)  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jacs.1c05859

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.202005479

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

<p>The perfectly diastereo- and enantiocontrolled catalytic synthesis of a cycloparaphenylene with four helical and two planar chiralities showing good chiroptical responses was achieved by the rhodium-catalyzed alkyne cyclotrimerization.</p>

DOI： 10.1039/d1sc00861g

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jacs.1c00887

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.1c00393

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ejoc.202100143

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acscatal.0c05394

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

<title>Abstract</title>It has been established that the dienylation of unfunctionalized arenes with 1,6-diynes, possessing aryl groups at the diyne termini, proceeds to give the corresponding dienylated arenes in the presence of a catalytic amount of an electron-deficient cyclopentadienyl rhodium(III) complex, [CpERhCl2]2, and a stoichiometric amount of silver carbonate. Experimental and theoretical mechanistic studies revealed that a CpERh(I) complex generated in situ might catalyze the present dienylation­ reaction.

DOI： 10.1055/a-1328-6436

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Language：English   Publishing type：Research paper (scientific journal)  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/CL.200609

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.0c02499

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DOI： 10.1002/chem.202001450

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DOI： 10.1002/anie.202006959

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DOI： 10.1002/anie.202003009

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.202003009

Language：English   Publishing type：Research paper (scientific journal)  

Planar chiral zigzag-type [8]- and [12]cyclophenylene (CP) belts have been synthesized in good yields with high ee values of 98% and 83%, respectively, by the rhodium-catalyzed enantioselective intramolecular sequential cyclotrimerizations of the corresponding cyclic polyynes. The observed high enantioselectivity arises from the regioselective formation of a rhodacycle intermediate from an unsymmetric triyne unit. The X-ray crystal structural analysis of the racemic planar chiral zigzag-type [8]CP belt revealed that the uneven molecules mesh with each other to form a one-dimensional columnar packing structure, in which one column contains single enantiomers, giving two types of chiral columns [(S)- and (R)-form columns] arranged alternately. The ring strain of the zigzag-type [8]CP belt was smaller than that of the armchair-type [8]CPP belt despite its smaller ring size, due to the presence of the strain-relieving m-terphenyl moieties. The effect of the number of the benzene rings of the zigzag-type CP belts on absorption and emission peaks was small due to interruption of π-conjugation at the m-phenylene moieties. However, the bending effect on the absolute fluorescence quantum yield as well as absorption and emission peaks was significant. Concerning chiroptical properties, the modest anisotropy dissymmetry factors of ECD and CPL were observed in the [8]CP belt.

DOI： 10.1021/jacs.0c03684

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ange.202003009

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Language：English   Publishing type：Research paper (scientific journal)  

An S-shaped double helicene-like molecule (>99 % ee), possessing stable helical chirality, has been synthesized by the rhodium(I)/difluorphos complex-catalyzed highly diastereo- and enantioselective intramolecular double [2+2+2] cycloaddition of a 2-naphthol- and benzene-linked hexayne. The collision between two terminal naphthalene rings destabilizes the helical chirality of the S-shaped double helicene-like molecule, but the introduction of two additional fused benzene rings significantly increases the configurational stability. Thus, no epimerization and racemization were observed even at 100 °C. The enantiopure S-shaped double helicene-like molecule forms a trimer through the multiple C-H⋅⋅⋅π and C-H⋅⋅⋅O interactions in the solid-state. The trimers stack to form columnar packing structures, in which neighboring stacks have opposite dipole directions. The accumulation of helical structures in the same direction in the S-shaped double helicene-like molecule enhanced the chiroptical properties.

DOI： 10.1002/anie.202001794

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Language：English   Publishing type：Research paper (scientific journal)  

It has been established that a newly developed cyclopentadienyl rhodium(III) [CpA RhIII ] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho-bromination of O-phenyl carbamates with N-bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the CpA ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the CpA ligand and the carbonyl group of NBS.

DOI： 10.1002/chem.202000253

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-VCH Verlag  

DOI： 10.1002/chem.201905519

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-VCH Verlag  

DOI： 10.1002/chem.202000010

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Language：Japanese   Publishing type：Research paper (conference, symposium, etc.)  

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