Rh(III)‐Catalyzed Cross Dehydrogenative Coupling of <i>N</i>‐Phenyl Substituent with Thiophenes

Wei, Wen-Yi; Gong, Zi-Rong; Chai, Xinyu; Xu, Yan‐Jun; Dong, Lin

doi:10.1002/ejoc.202300294

Eur J Org Chem

2023

DOI: 10.1002/ejoc.202300294

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Rh(III)‐Catalyzed Cross Dehydrogenative Coupling of N‐Phenyl Substituent with Thiophenes

Wen-Yi Wei

Zi-Rong Gong

Xinyu Chai

et al.

Abstract: Rhodium(III)‐catalyzed cross‐dehydrogenative coupling involves a highly efficient C−C bond formation from N‐phenyl‐7‐azaindole frameworks, thiophenes. Various novel 7‐azaindole derivatives have been successfully developed with good substrate applicability.

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Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Zhang,

Luo,

Wang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryA Ru(II)‐catalyzed ortho allylation reaction of N‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This reaction is an effective pathway for synthesizing 7‐azaindole derivatives with a wide scope of substrates and high yields. In addition, the method can be extended to the allylation of other heterocyclic compounds and several cyclic carbonates, highlighting the practicality of this strategy for synthesis.This article is protected by copyright. All rights reserved.

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Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Zhang,

Luo,

Wang

et al. 2024

Chin. J. Chem.

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Research Progress of Rhodium(III)‐Catalyzed C(sp²)−H Bond Functionalization

Chen,

Dong,

Qiu

et al. 2025

Eur J Org Chem

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Over the past decade, rhodium‐catalyzed C‐H bond activation reactions have made significant progress and found broad applications in organic synthesis, biomedicine, and materials science. This is primarily attributed to their broad substrate scope, excellent functional group compatibility, and high reactivity. Currently, although considerable progress has been made, rhodium‐catalyzed C(sp2)‐H functionalization still heavily relies on directing groups to achieve selectivity, which significantly diminishes the reaction's efficiency. Additionally, the challenge of selectively functionalizing remote (meta/para) C‐H bonds further complicates research in this field. In this review, we primarily focus on the research progress in rhodium‐catalyzed C(sp2)‐H functionalization from 2018 to 2024, categorizing reactions by type and providing a systematic overview of the mechanistic insights for each.

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Rh(III)‐Catalyzed Cross Dehydrogenative Coupling of N‐Phenyl Substituent with Thiophenes

Abstract: Rhodium(III)‐catalyzed cross‐dehydrogenative coupling involves a highly efficient C−C bond formation from N‐phenyl‐7‐azaindole frameworks, thiophenes. Various novel 7‐azaindole derivatives have been successfully developed with good substrate applicability.

Cited by 2 publications

References 67 publications

Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Research Progress of Rhodium(III)‐Catalyzed C(sp²)−H Bond Functionalization

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Rh(III)‐Catalyzed Cross Dehydrogenative Coupling of N‐Phenyl Substituent with Thiophenes

Abstract: Rhodium(III)‐catalyzed cross‐dehydrogenative coupling involves a highly efficient C−C bond formation from N‐phenyl‐7‐azaindole frameworks, thiophenes. Various novel 7‐azaindole derivatives have been successfully developed with good substrate applicability.

Cited by 2 publications

References 67 publications

Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Research Progress of Rhodium(III)‐Catalyzed C(sp2)−H Bond Functionalization

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Research Progress of Rhodium(III)‐Catalyzed C(sp²)−H Bond Functionalization