期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 8, 页码 2866-2869出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510973
关键词
alkynylation; cyanation; cyclobutanol; manganese catalysis; ring-opening
资金
- Soochow University
- National Natural Science Foundation of China [21402134]
- Natural Science Foundation of Jiangsu Province [BK20140306]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
A novel C-C bond-forming strategy employing manganese-catalyzed ring-opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the g-position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring-opening of cyclobutanol substrates by C-C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical-mediated C-S bond cleavage.
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