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Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.

ABSTRACT: 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 (PhSiH3 ) 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.

SUBMITTER: Qin T

PROVIDER: S-EPMC5295468 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.

Qin Tian T Malins Lara R LR Edwards Jacob T JT Merchant Rohan R RR Novak Alexander J E AJ Zhong Jacob Z JZ Mills Riley B RB Yan Ming M Yuan Changxia C Eastgate Martin D MD Baran Phil S PS

Angewandte Chemie (International ed. in English) 20161216 1

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<sub>3</sub> ) or an electron-deficient olefin. These reactions feature operational simplicity, inexpe ...[more]

PMID: 27981703

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