Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 24, Pages 6994-6998Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201702833
Keywords
alkynes; cross-coupling; gold; hypervalent compounds; reaction mechanisms
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Funding
- National Key Research and Development Program [2016YFA0202900]
- National Natural Science Foundation of China [21372244, 21572256, 21421091]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
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A new and efficient method for the synthesis of unsymmetrical 1,3-butadiynes by gold-catalyzed C(sp)-C(sp) cross-coupling of terminal alkynes with alkynyl hypervalent iodine(III) reagents has been developed. The reaction features high selectivity and efficiency, mild reaction conditions, wide substrate scope, and functional-group compatibility, and is a highly attractive complement to existing methods. Mechanistic studies reveal that formation of a phenanthrolinyl-ligated gold(I) complex is crucial for the efficiency and selectivity of the target transformation.
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