期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 1, 页码 304-309出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908466
关键词
boronate esters; borylation; cross-coupling; diboration; halogenation
资金
- China Scholarship Council
We report herein the catalytic triboration of terminal alkynes with B(2)pin(2) (bis(pinacolato)diboron) using readily available Cu(OAc)(2) and (PBu3)-Bu-n. Various 1,1,2-triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP-2) inhibitors, were obtained directly in moderate to good yields. The process features mild reaction conditions, a broad substrate scope, and good functional group tolerance. This copper-catalyzed reaction can be conducted on a gram scale to produce the corresponding 1,1,2-triborylalkenes in modest yields. The utility of these products was demonstrated by further transformations of the C-B bonds to prepare gem-dihaloborylalkenes (F, Cl, Br), monohaloborylalkenes (Cl, Br), and trans-diaryldiborylalkenes, which serve as important synthons and have previously been challenging to prepare.
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