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Photoredox/Nickel‐Catalyzed Single‐Electron Tsuji–Trost Reaction: Development and Mechanistic Insights
Author(s) -
Matsui Jennifer K.,
GutiérrezBonet Álvaro,
Rotella Madeline,
Alam Rauful,
Gutierrez Osvaldo,
Molander Gary A.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809919
Subject(s) - regioselectivity , chemistry , catalysis , nickel , allylic rearrangement , oxidative addition , photochemistry , photoredox catalysis , combinatorial chemistry , computational chemistry , organic chemistry , photocatalysis
A regioselective, nickel‐catalyzed photoredox allylation of secondary, benzyl, and α‐alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DFT and DLPNO‐CCSD(T)] support the mechanistic hypothesis of a Ni 0 to Ni II oxidative addition pathway followed by radical addition and inner‐sphere allylation.
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