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Suzuki–Miyaura Type Regioselective C–H Arylation of Aromatic Aldehydes by a Transient Directing Strategy

Bao Chao, Chaolumen Bai, Yan He, Ruisheng Zhao, Dan Liu, Tegshi Muschin, Agula Bao, Chaolu Eerdun, Yong‐Sheng Bao

2023Organic Letters12 citationsDOI

Abstract

Herein, we disclose a common approach for palladium-catalyzed direct coupling of the ortho -C–H bond of aromatic aldehydes with various organoboronic reagents by a transient directing strategy. In contrast to widely used cross-coupling reactions of C–H bonds with aryl halides, which generally need silver salt as a halide removal reagent, the method which used BQ/TFA as weak oxidation system for the Pd II /Pd 0 redox cycle is cost-effective, ecofriendly, and more aligned with green catalysis. This broadly applicable method opens up a new and efficient Suzuki–Miyaura coupling route for the direct formation of carbon–carbon bonds by C–H bond activation.

Topics & Concepts

ChemistryReagentHalideRegioselectivityCatalysisArylAryl halidePalladiumCombinatorial chemistryOrganic synthesisOrganic chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions
Suzuki–Miyaura Type Regioselective C–H Arylation of Aromatic Aldehydes by a Transient Directing Strategy | Litcius