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Nickel/Photo-Cocatalyzed C(sp<sup>2</sup>)–H Allylation of Aldehydes and Formamides

Pei Fan, Rui Wang, Chuan Wang

2021Organic Letters26 citationsDOI

Abstract

)-H allylation of aldehydes and formamides wherein both allyl acetates and allyl alcohols can be used as the allylating agents. In this reaction, radical-type umpolung of the formyl moiety is enabled by tetrabutylammonium decatungstate as a hydrogen-atom-transfer photocatalyst, whereas nickel serves to cleave the C-O bond of allyl acetates or allyl alcohols. The synergistic effect of these two catalysts provides new access to various β,γ-unsaturated ketones and amides with high selectivities.

Topics & Concepts

FormamidesChemistryUmpolungCatalysisMoietyNickelPhotocatalysisPhotochemistryMedicinal chemistryOrganic chemistryNucleophileCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
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