Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 30, Pages 7870-7874Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402475
Keywords
cross-coupling; gold; homogeneous catalysis; oxygen heterocycles; synthetic methods
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Funding
- National Basic Research Program of China (973 Program) [2011CB808601]
- National NSF of China [21202105, 21025205, 21321061, J1310008, J1103315J0104]
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In sharp contrast to the gold-catalyzed reactions of alkynes/allenes with nucleophiles, gold-catalyzed oxidative cross-couplings and especially C-H/C-H cross-coupling have been under represented. By taking advantage of the unique redox property and carbophilic pi acidity of gold, this work realizes the first gold-catalyzed direct C(sp(3))-H alkynylation of 1,3-dicarbonyl compounds with terminal alkynes under mild reaction conditions, with subsequent cyclization and in situ oxidative alkynylation. A variety of terminal alkynes including aryl, heteroaryl, alkenyl, alkynyl, alkyl, and cyclopropyl alkynes all successfully participate in the domino reaction. The protocol offers a simple and region-defined approach to 3-alkynyl polysubstituted furans.
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