Enamines as Surrogates of Alkene Carbanions for the Reductive Alkenylation of Secondary Amides: An Approach to Allylamines

Ai-E Wang*, Cun-Cun Yu, Ting-Ting Chen, Yong-Peng Liu and Pei-Qiang Huang*

*Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China, Email: aiewangxmu.edu.cn, pqhuangxmu.edu.cn

A.-E. Wang, C.-C. Yu, T.-T. Chen, Y.-P. Liu, P.-Q. Huang, Org. Lett., 2018, 20, 999-1002.

DOI: 10.1021/acs.orglett.7b03943 (free Supporting Information)

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Abstract

A reductive alkenylation of secondary amides with enamines provides allylamines using trifluoromethanesulfonic anhydride as an amide activation reagent and enamines as unconventional alkenylation reagents.

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proposed mechanism

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Key Words

allylamines, sodium borohydride

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ID: J54-Y2018