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Updated: May 8, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Deaminative C(sp3)─C(sp3) Cross-Coupling of Benzylamines with Alcohols and Carboxylic Acids via Radical Sorting
William Y Zhao1, Noriyuki Takanashi1, Albert Cabré2
1Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
Abstract:
Benzylamines represent a promising yet underexplored class of building blocks in C(sp3)─C(sp3) bond formation. The scarcity of deaminative coupling methods of benzylamines with other ubiquitous native functionalities, such as alcohols and carboxylic acids, has constrained their synthetic utility. Herein, we report two metallaphotoredox C(sp3)─C(sp3) cross-coupling reactions that merge structurally diverse benzylamines with carboxylic acids and 3° alcohols. In both transformations, the key bond-forming step proceeds via a Fe-porphyrin-catalyzed SH2 radical sorting pathway. Both reactions exhibit broad substrate scope, with their synthetic utility further highlighted in the synthesis of complex, biologically active compounds, semisaturated aromatic scaffolds, and enantiopure pyrrolidine derivatives.
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