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Wei F, Zhou T, Ma Y, et al. Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles. Org Lett. 2017;19(8):2098-2101doi: 10.1021/acs.orglett.7b00701.
Wei, F., Zhou, T., Ma, Y., Tung, C. H., & Xu, Z. (2017). Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles. Organic letters, 19(8), 2098-2101. https://doi.org/10.1021/acs.orglett.7b00701
Wei, Fang, et al. "Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles." Organic letters vol. 19,8 (2017): 2098-2101. doi: https://doi.org/10.1021/acs.orglett.7b00701
Wei F, Zhou T, Ma Y, Tung CH, Xu Z. Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles. Org Lett. 2017 Apr 21;19(8):2098-2101. doi: 10.1021/acs.orglett.7b00701. Epub 2017 Apr 07. PMID: 28387509.
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Org Lett. 2017 Apr 21;19(8):2098-2101. doi: 10.1021/acs.orglett.7b00701. Epub 2017 Apr 07.

Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles.

Organic letters

Fang Wei, Tong Zhou, Yudao Ma, Chen-Ho Tung, Zhenghu Xu

Affiliations

  1. Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University , Jinan 250100, P. R. China.
  2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.

PMID: 28387509 DOI: 10.1021/acs.orglett.7b00701

Abstract

Metalated triazoles are the key reactive intermediate of the current click reaction (CuAAC). Bench-stable 5-stannyl triazoles are obtained by a copper-catalyzed interrupted click reaction of easily available terminal alkynes. Subsequent palladium-catalyzed cross-coupling reactions, electrophilic trifluoromethylthiolation and trifluoromethylation, generate diverse 1,4,5-trisubstituted triazoles efficiently, which the traditional click reaction is unable to do.

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