Issue 11, 2024

Copper-catalyzed oxidative sulfenylation and alkylation of indolin-2-ones for direct construction of sulfur-substituted quaternary carbons

Abstract

The selective functionalization of ubiquitous C(sp3)–H bonds for constructing complex molecules is a highly sought-after method in academia as well as the chemical industry. In particular, it is rather challenging to install two different kinds of substituent groups into one reaction site in a one-pot process. To aid in this effort, we have developed a one-pot reaction for the construction of S-substituted quaternary carbon centers starting from secondary C(sp3)–H substrates. A sulfenylation and alkylation procedure catalyzed by simple copper salts has been established. It provides a rapid access to C3-alkylated 3-thioxyindolin-2-ones from abundant feedstock chemicals and features operational simplicity, broad substrate scope and good functional group compatibility.

Graphical abstract: Copper-catalyzed oxidative sulfenylation and alkylation of indolin-2-ones for direct construction of sulfur-substituted quaternary carbons

Supplementary files

Article information

Article type
Research Article
Submitted
18 Mar 2024
Accepted
10 Apr 2024
First published
12 Apr 2024

Org. Chem. Front., 2024,11, 3131-3136

Copper-catalyzed oxidative sulfenylation and alkylation of indolin-2-ones for direct construction of sulfur-substituted quaternary carbons

Y. Zhang, Y. Wang, Z. Liu, S. Zheng, G. Li, D. Feng and D. Xu, Org. Chem. Front., 2024, 11, 3131 DOI: 10.1039/D4QO00491D

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