Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 34, Pages 10069-10073Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604898
Keywords
alkenes; halogenation; organoboron; oxidation; trifluoromethylation
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Funding
- 1000-Youth Talents Plan
- Sun Yat-sen University
- State Key Laboratory of Natural and Biomimetic Drugs [K20150215]
- National Natural Science Foundation of China [81402794, 21472250]
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The synthesis of halogenated and trifluoromethylated alpha-boryl ketones via a one-pot oxidative difunctionalization of alkenyl MIDA boronates is reported. These novel densely functionalized organoborons bearing synthetically and functionally valuable carbonyl, halogen/CF3 and boronate moieties within the same molecule are synthetically challenging for the chemist, but have great synthetic potential, as demonstrated by their applications in a straightforward synthesis of borylated furans. The generality of this reaction was extensively investigated. This reaction is attractive since the starting materials, alkenyl MIDA boronates, are easily accessible.
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