期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 3, 页码 1201-1205出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913062
关键词
carboxylic acid; diarylation; nickel; trifunctionalization
资金
- Bristol-Myers Squibb
- National Science Foundation [CHE-1800280]
- Alfred P. Sloan Fellowship Program
- Camille Dreyfus Teacher-Scholar Program
- NSF [DGE-1346837]
- Kwanjeong Educational Foundation
A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate group.
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