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Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides

Ming-Hui Zhu, Cheng-Long Yu, Ya-Lan Feng, Muhammad Usman, Dayou Zhong, Xin Wang, Nasri Nesnas, Wen-Bo Liu*

*College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072, China, Email: wenboliuwhu.edu.cn

M.-H. Zhu, C.-L. Yu, Y.-L. Feng, M. Usman, D. Zhong, X. Wang, N. Nesnas, W.-B. Liu, Org. Lett., 2019, 21, 7073-7077.

DOI: 10.1021/acs.orglett.9b02639 (free Supporting Information)


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Abstract

A consecutive detosylation/alkylation transformation of tosylated indoles and phenols with alkoxides/alcohols as the alkylation reagents features mild reaction conditions, high ipso-selectivity, and good functional group tolerance. A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized.

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Key Words

indoles, N-alkylation, N-benzylation, aryl ethers


ID: J54-Y2019