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J Org Chem. 2017 May 19;82(10):5294-5300. doi: 10.1021/acs.joc.7b00627. Epub 2017 May 10.

From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles.

The Journal of organic chemistry

Kai Huang, Guorong Sheng, Ping Lu, Yanguang Wang

Affiliations

  1. Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.

PMID: 28474887 DOI: 10.1021/acs.joc.7b00627

Abstract

An efficient and highly regioselective synthesis of 1-allenyl-5-aryl-1,2,3-triazoles from 1-sulfonyl-4-aryl-1,2,3-triazoles is disclosed. 1-Sulfonyl-4-aryl-1,2,3-triazoles reacted with propargylic alcohols in the presence of trifluoroboron etherate to furnish 1-allenyl-5-aryl-1,2,3-triazoles. When secondary alcohols were used as substrate, the outcome of the reaction was 1-alkyl-5-aryl-1,2,3-triazoles.

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