Chiral Primary Amine-Catalyzed Asymmetric Photochemical Reactions of Pyridotriazoles with Boronic Acids to Access Triarylmethanes

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 29, 2025

Imine-containing azaarene-based triarylmethanes are vital molecular motifs that prevalent in a wide array of bioactive compounds. Recognizing the limitations current synthetic methodologies─marked by scarcity examples and difficulties flexible functional group modulation─we have developed an efficient modular asymmetric photochemical strategy employing pyridotriazoles boronic acids as substrates. Utilizing novel chiral diamine-derived pyrroles primary amines catalysts, we successfully synthesized diverse range with high yields excellent enantioselectivities. This method not only exhibits broad substrate scope outstanding tolerance but also enables precise synthesis deuterated derivatives using inexpensive D2O deuterium source. Mechanistic studies reveal unusual 1,4-boron shift is critical step generating boronated enamine intermediate, while shedding light on potential enantiocontrol mechanisms facilitated catalyst.

Language: Английский

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Chiral Bis(binaphthyl) Cyclopentadienyl Ligands for Rhodium-Catalyzed Desymmetrization of Diarylmethanes via Selective Arene Coordination

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

Owing to substantial advances in the past several decades, transition-metal-catalyzed asymmetric reactions have garnered considerable attention as pivotal methods for constructing chiral molecules from abundant, readily available achiral counterparts. These are largely attributed development of ligands that control stereochemistry through steric repulsion and other noncovalent interactions between functional groups or prochiral centers on substrates. However, stereocontrol weakens dramatically with increasing distance reaction site group center. Herein, we report a symphonic strategy remote Rh(III)-catalyzed benzylic C-H bond addition diarylmethanes which two aryl motifs differ at

Language: Английский

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Rhodium‐Catalyzed C(sp³)–H Arylation of 8‐Methylquinolines with Arylsilanes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2627 - 2632

Published: July 9, 2024

Comprehensive Summary We herein describe a Cp*Rh III ‐catalyzed C(sp 3 )–H mono‐arylation of 8‐methylquinolines with benign arylsilanes. The use 1‐adamantane carboxylic acid can benefit the efficiency in this transformation, and AgF was both activator reoxidant. Control experiments indicated inability C—H cleavage determining rate reaction.

Language: Английский

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Rh-Catalyzed Functionalization of N-Heterocycles Through C–H Activation

Topics in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 89 - 157

Published: Jan. 1, 2024

Language: Английский

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