Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 45, Pages 16837-16840Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja409533s
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Funding
- ICIQ Foundation
- Spanish Government [CTQ2011-25418]
- Osaka Prefecture University
- Grants-in-Aid for Scientific Research [25105745] Funding Source: KAKEN
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Exceedingly facile (23 degrees C) and chemoselective H-CF3 activation with [(dppp)Pd(Ph)(OH)] in the presence of a Lewis base promoter such as n-Bu3P leads to Pd-CF3 bond formation in nearly quantitative yield. A combined experimental and computational study points to a new mechanism that involves H-bonding Pd-O(H)center dot center dot center dot H-CF3 and nucleophilic attack of the promoter on the metal, followed by a push-pull-type collapse of the resultant five-coordinate Pd(II) intermediate via a polar transition state.
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