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A Method for Bischler-Napieralski-Type Synthesis of 3,4-Dihydroisoquinolines

Lin Min, Weiguang Yang, Yunxiang Weng, Weiping Zheng, Xinyan Wang*, Yuefei Hu*

*Department of Chemistry, Tsinghua University, Beijing 100084, P.R. China, Email: wangxinyanmail.tsinghua.edu.cn, yfhmail.tsinghua.edu.cn

L. Min, W. Yang, Y. Weng, W. Zheng, X. Wang, Y. Hu, Org. Lett., 2019, 21, 2574-2577.

DOI: 10.1021/acs.orglett.9b00534 (free Supporting Information)


Abstract

Tf2O promotes a Bischler-Napieralski-type synthesis of 3,4-dihydroisoquinolines from phenylethanols and nitriles via a tandem annulation, in which a phenonium ion as a stable and reactive primary phenylethyl carbocation is formed.

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proposed mechanism



Key Words

Bischler-Napieralski Reaction, 3,4-Dihydroisoquinolines


ID: J54-Y2019