期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 8, 页码 3054-3061出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900053b
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资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Merck Frosst Center for Therapeutic Research for an Industrial Research Chair
- University of Toronto
[GRAPHICS] A highly efficient water-accelerated palladium-catalyzed reaction of gem-dibromoolefins with a boronic acid via a tandem Suzuki-Miyaura coupling and direct arylation is reported. A wide range of aryl, alkenyl, and alkyl boronic acids, as well as a variety of substitution patterns on the phenyl ring, are tolerated. Additionally, mechanistic studies were conducted to ascertain the order of the couplings as well as the role(s) of water. Results from this study indicate that the major pathway is a Suzuki-Miyaura coupling/direct arylation sequence and that water accelerates the Pd(0) formation and Suzuki-Miyaura coupling.
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