期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 46, 页码 14284-14288出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608090
关键词
boron; C-C activation; cyclization; sulfur; sulfur heterocycles
资金
- NIH [1R01GM098512-01]
- University of California, Irvine
- Allergan Foundation Graduate Fellowship
The first ring-forming thioboration reaction of C-C pi bonds is reported. This catalyst-free method proceeds in the presence of a commercially available external electrophilic boron source (B-chlorocatecholborane) in good to high yields. The method is scalable and tolerates a variety of functional groups that are intolerant of other major borylation methods. The resulting borylated benzothiophenes participate in a variety of in situ derivatization reactions, showcasing that these borylated intermediates do not need to be isolated prior to downstream functionalization. This methodology has been extended to the synthesis of borylated dihydrothiophenes. Mechanistic experiments suggest that the operative mechanistic pathway is through boron-induced activation of the alkyne followed by electrophilic cyclization, as opposed to S-B sigma bond formation, providing a mechanistically distinct pathway to the thioboration of C-C pi bonds.
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