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Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols. 2014
Pin Gao, and
Yong-Wen Shen, and
Ran Fang, and
Xin-Hua Hao, and
Zi-Hang Qiu, and
Fan Yang, and
Xiao-Biao Yan, and
Qiang Wang, and
Xiang-Jun Gong, and
Xue-Yuan Liu, and
Yong-Min Liang
State key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China).
A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.
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