Journal
CHEMCATCHEM
Volume 8, Issue 19, Pages 3112-3117Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201600811
Keywords
alkynes; C-C coupling; ketones; nucleophilic addition; phosphorus
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Funding
- National Basic Research Program of China (973) [2015CB856603]
- National Natural Science Foundation of China [20472096, 21372241, 21361140350, 20672127, 21102166, 21121062, 21302203, 21421091, 20732008, 21572052]
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The formerly unexplored delta-carbon of alkynones could be activated as a nucleophilic reaction site and trapped by electron-deficient carbonyl-group-containing compounds upon phosphine catalysis, which provided three kinds of delta-addition and isomerization products in moderate to excellent yields. Plausible mechanisms were proposed on the basis of deuteri-um-labeling experiments. Thus, a novel strategy for phosphine-catalyzed delta-carbon addition of alkynones to electron-deficient carbonyl groups was developed, affording the corresponding substituted 3,5-dien-2-one derivatives under mild conditions.
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