Palladium Catalyzed Direct Carbonylative Thiomethylation of Aryldiazonium Salts and Amines with 4-(Methylthio)-2-Butanone as (Methylthio) Transfer Agent

Qingqiang Tian; Shasha Xu; Chiying Zhang; Xinyi Liu; Xiangwei Wu; Yahui Li

doi:10.1021/acs.joc.1c00665

Palladium Catalyzed Direct Carbonylative Thiomethylation of Aryldiazonium Salts and Amines with 4-(Methylthio)-2-Butanone as (Methylthio) Transfer Agent

J Org Chem. 2021 Jul 2;86(13):8797-8804. doi: 10.1021/acs.joc.1c00665. Epub 2021 Jun 18.

Authors

Qingqiang Tian¹, Shasha Xu¹, Chiying Zhang¹, Xinyi Liu¹, Xiangwei Wu¹, Yahui Li^{1

2}

Affiliations

¹ Key Laboratory of Agri-Food Safety of Anhui Province, School of Resources and Environment, Anhui Agricultural University, Hefei 230036, China.
² State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bio-engineering, Ministry of Education, Guizhou University, Guiyang 550025, China.

PMID: 34142838
DOI: 10.1021/acs.joc.1c00665

Abstract

Herein, an interesting palladium-catalyzed procedure for the direct carbonylative thiomethylation of aromatic amine derivatives with 4-methylthio-2-butanone is developed. Using 4-methylthio-2-butanone as (methylthio) transfer agent, a variety of corresponding thioesters are obtained with moderate to good yields under base-free condition. In addition, good functional group tolerance can be observed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines*
Butanones
Catalysis
Palladium*
Salts

Substances

Amines
Butanones
Salts
Palladium
methylethyl ketone