Rhodium-Catalyzed Asymmetric C–H Functionalization Reactions

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(16), P. 10079 - 10134

Published: Aug. 1, 2023

This review summarizes the advancements in rhodium-catalyzed asymmetric C–H functionalization reactions during last two decades. Parallel to rapidly developed palladium catalysis, rhodium catalysis has attracted extensive attention because of its unique reactivity and selectivity reactions. In recent years, Rh-catalyzed have been significantly many respects, including catalyst design, reaction development, mechanistic investigation, application synthesis complex functional molecules. presents an explicit outline catalysts ligands, mechanism, scope coupling reagents, applications.

Language: Английский

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Rh(III)-Catalyzed Atroposelective C–H Selenylation of 1-Aryl Isoquinolines

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(8), P. 6009 - 6015

Published: April 5, 2024

Rhodium(III)-catalyzed atroposelective C–H selenylation of 1-aryl isoquinolines has been achieved. The direct reaction between and 2-(phenylselanyl)isoindoline-1,3-dione in the presence chiral SCpRh(III) complex afforded a series axially isoquinoline selenides up to 95% yield 96% ee. features mild conditions broad substrate scope. DFT calculations revealed that C–Se bond formation step proceeds through formal SN2 pathway.

Language: Английский

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Chiral Cp^xRhodium(III)‐Catalyzed Enantioselective Aziridination of Unactivated Terminal Alkenes

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(12)

Published: Jan. 27, 2024

Chiral cyclopentadienyl-rhodium(III) Cp

Language: Английский

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Enantioselective synthesis of indenols via rhodium(III)–catalyzed C-H activation/annulation of ketones with alkynes

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

Language: Английский

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Planar-Chiral Cyclopentadienyl Rhodium Catalysts: Design Concept, Chiral Resolution Strategy, and Applications

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(15), P. 10468 - 10473

Published: July 26, 2023

Chiral half-sandwich cyclopentadienyl rhodium(III) (CpRhIII) complexes are potent catalysts for asymmetric C–H activation. They primarily produced from chiral Cp ligands bearing diverse backbones. However, it remains a big challenge to develop planar-chiral CppxRhIII with prochiral (Cppx) due the lack of design guidelines and ideal resolution methods. To solve this problem, we present herein feasible concept robust strategy. Notably, type catalyst tetrasubstituted Cppx formula C5HMe2PhAr has been successfully developed by routine silica-gel chromatographic separation related diastereomeric diene derivatives. This proved be highly effective activations, including reaction N-methoxybenzamides 1,4-benzoquinone (up 92% yield, 96% ee) O-Boc hydroxamates norbornene 94% ee).

Language: Английский

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Recent Progress in Metal-Catalyzed Asymmetric Hydroarylation of Internal Alkenes Through C—H Cleavage

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 546 - 546

Published: Jan. 1, 2025

Language: Английский

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Application of Planar Chiral Cyclopentadienyl Rhodium Catalysts without Chiral Substituents in Asymmetric C—H Activation

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 466 - 466

Published: Jan. 1, 2025

Language: Английский

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[2.2]Benzoindenophane‐Based Chiral Indenyl Ligands: Design, Synthesis, and Applications in Asymmetric C−H Activation

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(32)

Published: May 23, 2024

Abstract Development of chiral indenyl ligands for asymmetric C−H activation is a longstanding challenge, and extremely few successes have been achieved. In this paper, we describe class readily accessible, facilely tunable user‐friendly featuring [2.2]benzoindenophane skeleton via divergent synthesis strategy. The corresponding rhodium catalysts were successfully applied in the reaction O‐Boc hydroxybenzamide with alkenes to give various dihydroisoquinolone products (up 97 % yield, up 98 ee). Moreover, carboxylic acids alkynes was also accomplished, providing range axially isocoumarins 99 94 Notably, represents first example enantioselective transition metal catalyzed C(sp 2 )−H activation/oxidative coupling benzoic internal construct isocoumarins. Given many attractive features ligands, such as convenient synthesis, high tunability exclusive face‐selectivity coordination, its applications more catalytic other catalysis are foreseen.

Language: Английский

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Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 466 - 485

Published: Sept. 6, 2023

Abstract Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d6-metal (CoIII, RhIII, IrIII, RuII)-catalyzed functionalization reactions. The review is categorized according type of metal catalyst and ligand employed. Representative enantio-determining models catalytic cycles are presented.

Language: Английский

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SCpRh(III)-Catalyzed Asymmetric C–H Trifluoromethylalkylation of N-Methoxybenzamides with β-Trifluoromethyl-α,β-Unsaturated Ketones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1501 - 1505

Published: Feb. 13, 2024

Asymmetric C–H trifluoromethylalkylation represents a novel and straightforward synthetic method for the construction of chiral CF3-containing compounds. However, reported examples remain limited, given challenges reactivity enantioselective control. Herein, we report SCpRh(III)-catalyzed asymmetric aryl alkenyl reaction with β-trifluoromethyl-α,β-unsaturated ketones. The CF3-bearing adducts were obtained in moderate to good yields high enantioselectivity (up 81% yield 96% ee). features mild conditions broad substrate scope. products could undergo diverse functional group transformations.

Language: Английский

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