Nickel‐Catalyzed Activation of Acyl C−O Bonds of Methyl Esters
Year: 2016
Type: article
Abstract: 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.
Institution: University of California, Los Angeles
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Funders: National Science Foundation, Alfred P. Sloan Foundation, Camille and Henry Dreyfus Foundation, Bristol-Myers Squibb, National Institutes of Health, University of California, Los Angeles, ACS Division of Organic Chemistry, National Institute of General Medical Sciences, National Center for Research Resources, Division of Chemistry, Institute for Digital Research and Education, University of California, Los Angeles
Awards: Acquisition of Upgraded NMR Instrumentation for Chemistry Research, Education and Training, G1661892572, G2679848640, G3042249484, G310123084, G401885085, Stereoselectivities of Synthetic Organic Reactions, Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical Research, XSEDE: eXtreme Science and Engineering Discovery Environment, STEREOSELECTIVITIES IN SYNTHETIC ORGANIC REACTIONS, G7435049567, G7579982596, G910930967, Development of Carbamate Amination Methodology and Synthesis of Levofloxacin
OpenAlex ID: W2263756718