Blue-light induced iron-catalyzed chemoselective α-alkylation and α-olefination of arylacetonitriles with alcohols†
*a
and
Weihui
Zhong
*a
Abstract
Alcohols and nitrile derivatives are highly important skeletons, widely applied in both organic and bioorganic chemistry. Borrowing hydrogen (BH) and dehydrogenative coupling (DC) strategies are powerful and environmentally friendly strategies for accessing α-alkyl nitriles and α,β-substituted acrylonitriles, owing to their atom economy and readily available starting materials. Herein, we have reported the first example of a mild and general protocol for the synthesis of α-alkyl nitriles and α,β-substituted acrylonitriles under photoirradiation. The reaction featured broad substrate scope with good functional group tolerance under simple conditions (43 examples, 50–88% yields). Remarkably, the mildness and practicality of this protocol were further demonstrated by the successful synthesis of anipamil via a two-cascade borrowing hydrogen procedure.
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