期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 24, 页码 7140-7145出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803668
关键词
1,3-enynes; allenyl nitriles; copper; radical reaction; regioselectivity
资金
- National Nature Science Foundation of China [21523005, 21472219, 21790331, 21761142010]
- National Basic Research Program of China (973) [2015CB856600]
- Science and Technology Commission of Shanghai Municipality [17QA1405200, 17JC1401200]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Key Research Program of Frontier Science of the Chinese Academy of Sciences [QYZDJSSW-SLH055]
- Research Grants Council of Hong Kong [HKUST16304416, HKUST-SBI16SC08]
- CAS Interdisciplinary Innovation Team
A ligand-controlled system that enables regioselective trifluoromethylcyanation of 1,3-enynes has been identified, which provides access to a variety of CF3-containing tri- and tetrasubstituted allenyl nitriles. We disclose that the involved propargylic radicals can be selectively trapped by (Box)Cu-II cyanide, while the tautomerized allenyl radicals are trapped by (phen)Cu-II cyanide (Box= bisoxazoline, phen=phenanthroline). In addition, the reaction features broad substrate scope and excellent functional group compatibility. Moreover, this protocol represents a novel regioselectivity-tunable functionalization of 1,3-enynes via radicals, which we believe will have great implications for the development of catalytic systems for selectivity control in radical and organometallic chemistry.
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