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1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Decomposition of Difluorocarbene and the Subsequent Trifluoromethylation

Jian Zheng, Jin-Hong Lin, Xiao-Yun Deng and Ji-Chang Xiao*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: jchxiaosioc.ac.cn

J. Zheng, J.-H. Lin, X.-Y. Deng, J.-C. Xiao, Org. Lett., 2015, 17, 532-535.

DOI: 10.1021/ol503548s


Abstract

Difluorocarbene derived from various carbene precursors could be effectively decomposed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) into a fluoride ion and carbon monoxide. This decomposition process was successfully combined with a trifluoromethylation of various (hetero)aryl iodides without the addition of an external fluoride ion.

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Key Words

trifluoromethylation


ID: J54-Y2015