Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 8, Pages 2810-2814Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511486
Keywords
C-O activation; density functional calculations; methyl esters; nickel catalysis; oxidative addition
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Funding
- Boehringer Ingelheina
- DuPont
- Bristol-Myers Squibb
- Camille and Henry Dreyfus Foundation
- A. P. Sloan Foundation
- UCLA Gold Shield Alumnae
- University of California, Los Angeles
- NIH-NIGMS [GM36700]
- NIH [F31 GM101951-02]
- ACS Division of Organic Chemistry
- Foote family
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We report the first catalytic method for activating the acyl C-O bonds of methyl esters through an oxidative-addition process. The oxidative-addition adducts, formed using nickel catalysis, undergo in situ trapping to provide anilide products. DFT calculations are used to support the proposed reaction mechanism, to understand why decarbonylation does not occur competitively, and to elucidate the beneficial role of the substrate structure and the Al(OtBu)(3) additive on the kinetics and thermodynamics of the reaction.
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