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Nickel‐Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms
Author(s) -
Qin Tian,
Malins Lara R.,
Edwards Jacob T.,
Merchant Rohan R.,
Novak Alexander J. E.,
Zhong Jacob Z.,
Mills Riley B.,
Yan Ming,
Yuan Changxia,
Eastgate Martin D.,
Baran Phil S.
Publication year - 2017
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.201609662
Subject(s) - decarboxylation , chemistry , catalysis , nickel , combinatorial chemistry , reagent , olefin fiber , organic chemistry
Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N ‐hydroxyphthalimide (NHPI) based redox‐active esters were found to be convenient starting materials for simple, thermal, Ni‐catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH 3 ) or an electron‐deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.