Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions

Shengzhen Zhu; Yu Zhang; Jinyue Luo; Fei Wang; Xiaoji Cao; Shenlin Huang

doi:10.1039/C9GC04155A

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Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions†

Shengzhen Zhu,

^a Yu Zhang,

^a Jinyue Luo,^a Fei Wang,^a Xiaoji Cao^b and Shenlin Huang

*^a

Author affiliations

* Corresponding authors

^a Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College of Chemical Engineering, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing, P. R. China
E-mail: shuang@njfu.edu.cn

^b College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Rd, Hangzhou, Zhejiang 310014, P.R. China

Abstract

A sustainable and regioselective synthesis of highly functionalized indole-based sulfides from thiols and 2-indolymethanols is described. Notably, this reaction can be performed in the presence of 5 mol% In(OTf)₃ under aqueous micellar conditions using an inexpensive surfactant DBSA. This protocol offers several advantages including excellent regioselectivities, being organic solvent-free, ease of scale-up, broad substrate scope, and recycling of the aqueous reaction medium and catalyst.

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Article information

DOI: https://doi.org/10.1039/C9GC04155A
Article type: Communication
Submitted: 04 Dec 2019
Accepted: 15 Jan 2020
First published: 15 Jan 2020

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Green Chem., 2020,22, 657-661

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Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions

S. Zhu, Y. Zhang, J. Luo, F. Wang, X. Cao and S. Huang, Green Chem., 2020, 22, 657 DOI: 10.1039/C9GC04155A

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Green Chemistry

Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions†

Abstract

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Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions

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