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- Title
Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.
- Authors
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.
- 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.
- Subjects
DECARBOXYLATION; ORGANIC synthesis; REDOX polymers; HYDROGEN atom; ALKENES
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 1, p260
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201609662