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Chromium-Catalyzed Linear-Selective Alkylation of Aldehydes with Alkenes

Yuki Hirao, Yuri Katayama, Harunobu Mitsunuma, Motomu Kanai

2020Organic Letters55 citationsDOI

Abstract

We developed a chromium-catalyzed, photochemical, and linear-selective alkylation of aldehydes with alkylzirconium species generated in situ from a wide range of alkenes and Schwartz’s reagent. Photochemical homolysis of the C–Zr bond afforded alkyl radicals, which were then trapped by a chromium complex catalyst to generate the alkylchromium(III) species for polar addition to aldehydes. The reaction proceeded with high functional group tolerance at ambient temperature under visible-light irradiation.

Topics & Concepts

ChemistryHomolysisAlkylationChromiumCatalysisReagentPhotochemistryRadicalAlkylOrganic chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions
Chromium-Catalyzed Linear-Selective Alkylation of Aldehydes with Alkenes | Litcius