Rhodium/N‐Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp<sup>2</sup> and sp<sup>3</sup> CH Bonds with Chelation Assistance

Kim, Min; Kwak, Jaesung; Chang, Sukbok

doi:10.1002/anie.200903500

Cited by 153 publications

(12 citation statements)

References 57 publications

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“…However,a dvances in metal-complex-mediated reactions over the past decade have overcome many of thesedifficulties, with directing-group-assisted CÀHa ctivationh aving become particularly common. After the breakthrough report of ruthenium-catalyzed ketone-directed ortho-CÀHa ctivation by Murai et al in 1993, [5a] many functional groups,i ncluding ketones, [5] aldehydes, [6] carboxylic acids, [7] hydroxyls, [8] imines, [9] oximes, [10] amides, [11] anilides, [12] and nitrogen heterocycle [13] functional groups,among others, [14] have been used in this regard.…”

Section: Coordination-assisted Càhbond Activationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed π‐Bond‐Assisted CH Bond Functionalization: An Emerging Trend in Organic Synthesis

Gandeepan

2015

Chemistry An Asian Journal

174

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Transition-metal-catalyzed C - H activation is considered to be an important tool in organic synthesis and has been accepted and widely used by chemists because it is straightforward, cost-effective, and environmentally friendly. A variety of functional groups have been used to direct metal complexes and achieve regioselective C - H activation. Most directing is achieved through the σ-bond coordination of functional groups to the metal catalyst, followed by ortho-selective C - H bond cleavage. However, recent work has demonstrated that π-coordinating functional groups can also assist in guiding metal complexes for site-selective C - H bond activation. This emerging approach significantly expands the scope of C - H activation reactions in organic synthesis. Herein, recent developments in this field are summarized.

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Section: Coordination-assisted Càhbond Activationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed π‐Bond‐Assisted CH Bond Functionalization: An Emerging Trend in Organic Synthesis

Gandeepan

2015

Chemistry An Asian Journal

174

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“…10-[4-(Trifluoromethyl)phenyl]benzo[h]quinoline ( 10d ) [ 48 ]. Yellow oil (16 mg, 0.0495 mmol, 20%).…”

Section: Methodsmentioning

confidence: 99%

Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines

et al. 2018

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The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C–H activation and C–C coupling of 2-arylpyridines with triorganoindium reagents under Rh(I) catalysis is reported. Under the optimized conditions, we found that Me3In and Ar3In reagents reacted with 2-arylpyridines and related compounds in the presence of Rh(PPh3)3Cl, in PhCl/THF (9:1), at 120 °C for 48 h, to afford the ortho-coupling products in moderate to good yields. The nitrogen atom in the pyridine ring acts as a directing group to assist the functionalization at the ortho position of the aryl group forming a new C–C bond at this position.

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“…However, selective monoarylation of 8-methyl quinoline not reported (Scheme 5). [25] In 2016, Glorius and coworkers disclosed another reaction for the synthesis of enantioselective triarylmethanes. This time synthesis achieved by using Rh(I)-catalyst with chiral NHC ligand which provides the enantioselective triaryl compounds by controlling the steric and electronic nature of NHC ligands.…”

Section: Rh(i)-catalyzed C(sp )à H Functionalization Of 8-methylquinomentioning

confidence: 99%

Rhodium‐Catalyzed Selective C−H Bond Functionalization of Quinolines

et al. 2020

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In the last two decades, rhodium-based catalysts have been used extensively for the sp 2 and sp 3 CÀ H bond activation/functionalization of various arenes, heteroarenes, and aliphatic compounds, respectively. For quinoline functionalization rhodium has been used significantly as compared to other transition metals such as cobalt, copper, ruthenium, palladium and iridium. In this Minireview the progress on rhodium-catalyzed selective functionalization of quinoline N-oxides and 8-methylquinolines via sp 2 and sp 3 CÀ H bond activation, respectively have been highlighted. The main focus is on reaction mechanism, substrate scope, and positional selectivity.

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Rhodium/N‐Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp² and sp³ CH Bonds with Chelation Assistance

Cited by 153 publications

References 57 publications

Transition‐Metal‐Catalyzed π‐Bond‐Assisted CH Bond Functionalization: An Emerging Trend in Organic Synthesis

Transition‐Metal‐Catalyzed π‐Bond‐Assisted CH Bond Functionalization: An Emerging Trend in Organic Synthesis

Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines

Rhodium‐Catalyzed Selective C−H Bond Functionalization of Quinolines

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Rhodium/N‐Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp2 and sp3 CH Bonds with Chelation Assistance

Cited by 153 publications

References 57 publications

Transition‐Metal‐Catalyzed π‐Bond‐Assisted CH Bond Functionalization: An Emerging Trend in Organic Synthesis

Transition‐Metal‐Catalyzed π‐Bond‐Assisted CH Bond Functionalization: An Emerging Trend in Organic Synthesis

Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines

Rhodium‐Catalyzed Selective C−H Bond Functionalization of Quinolines

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Rhodium/N‐Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp² and sp³ CH Bonds with Chelation Assistance