Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 11-12, Pages 2141-2145Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200312
Keywords
C-C coupling; cycloalkanes; enynes; homogeneous catalysis; platinum
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Funding
- MICINN of Spain [CTQ2010-16790]
- MEC
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A new platinum-catalyzed cascade reaction that proceeds through an unusual cyclization pathway of enyne derivatives is described. This operationally simple, air-and moisture-tolerant reaction affords cycloalkyl ketone derivatives in a straightforward manner. The reaction can be considered as an unprecedented abnormal platinum-catalyzed cyclization of enynes. The role of the platinum catalyst promoting at least three different reactions in this auto-tandem catalytic process should also be remarked. The reaction also includes an unusual site-selective hydration of a practically symmetrical carbon-carbon triple bond directed by a hydroxy group. In this work we also describe the first platinum-catalyzed intramolecular hydroalkylation of an unactivated olefin with a simple dialkyl ketone.
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