在 Pummerer 型条件下用亚磺硫叶立德对吲哚进行直接双烷基化硫代反应。

Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions.

机构信息

Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.

出版信息

J Org Chem. 2022 Jan 21;87(2):1133-1143. doi: 10.1021/acs.joc.1c02502. Epub 2022 Jan 11.

DOI:10.1021/acs.joc.1c02502

PMID:35014848

Abstract

A base-free bis-alkyl thiolation reaction of indoles with sulfinothioates under Pummerer-type conditions is described. Sulfinothioates, activated with 2,2,2-trifluoroacetic anhydride, are demonstrated to be an efficient thiolation reagent for wide applications. This approach enabled double C-H thiolation at the C2 and C3 of the indole in one pot. The mechanism studies suggested the thiolation was realized through the sulfoxonium salt rather than sulfenyl carboxylate.

摘要

本文描述了在 Pummerer 型条件下吲哚与亚磺酰硫酯的无碱双烷基化硫代反应。用 2,2,2-三氟乙酐活化的亚磺酰硫酯被证明是一种用于广泛应用的有效硫代试剂。这种方法可以在一锅反应中实现吲哚的 C2 和 C3 位的双 C-H 硫代化。机理研究表明，硫代化是通过亚磺酰𬭩盐而不是磺酰基羧酸酯实现的。