Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 47, Pages 17068-17073Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910304
Keywords
alkene; borylation; carboboration; directing group; palladium
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Funding
- Bristol-Myers Squibb
- National Institutes of Health [5R35GM125052-02]
- Tsinghua University Department of Chemistry
- Nankai University College of Chemistry
- A. P. Sloan Foundation
- Dreyfus Foundation
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We report the development of palladium(0)-catalyzed syn-selective 1,2-carboboration and -silylation reactions of alkenes containing cleavable directing groups. With B(2)pin(2) or PhMe2Si-Bpin as nucleophiles and aryl/alkenyl triflates as electrophiles, a broad range of mono-, di-, tri- and tetrasubstituted alkenes are compatible in these transformations. We further describe a directed dearomative 1,2-carboboration of electron-rich heteroarenes by employing this approach. Through use of a removable chiral directing group, we demonstrate the viability of achieving stereoinduction in Heck-type alkene 1,2-difunctionalization. This work introduces new avenues to access highly functionalized boronates and silanes with precise regio- and stereocontrol.
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