期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 11, 页码 3579-3583出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813853
关键词
alkenes; boron; homogeneous catalysis; hydrocyanation; Lewis acids
资金
- Cluster of Excellence Unifying Concepts in Catalysis of the Deutsche Forschungsgemeinschaft [EXC 314/2]
- Berlin Graduate School of Natural Sciences and Engineering
- Einstein Foundation Berlin
A straightforward gram-scale preparation of cyclohexa-1,4-diene-based hydrogen cyanide (HCN) surrogates is reported. These are bench-stable but formally release HCN and rearomatize when treated with Lewis acids. For BCl3, the formation of the isocyanide adduct [(CN)BCl3](-) and the corresponding Wheland complex was verified by mass spectrometry. In the presence of 1,1-di- and trisubstituted alkenes, transfer of HCN from the surrogate to the C-C double bond occurs, affording highly substituted nitriles with Markovnikov selectivity. The success of this transfer hydrocyanation depends on the Lewis acid employed; catalytic amounts of BCl3 and (C6F5)(2)BCl are shown to be effective while B(C6F5)(3) and BF3OEt2 are not.
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