Work

Trifluoromethylthiolation Carbonylation of Unactivated Alkenes via Distal Migration

Year: 2024

Type: article

Abstract: Sulfur-containing compounds represent a significant category of organic compounds, and the introduction of sulfur groups into organic compounds can effectively enhance their biological activity and synthetic diversity. Although a variety of difunctionalization reactions of alkenes based on sulfur radicals have been documented, significant challenges remain in the carbonylative difunctionalization of unactivated alkenes by the addition of a sulfur radical. Herein, we present a trifluoromethylthiolative carbonylation reaction of unactivated alkenes, which goes through the addition of a trifluoromethylthiol radical to unactivated alkenes and then carbonylation of the newly generated carbon radical intermediate. A heterocyclic/aryl migration in the presence of carbon monoxide is crucial for the success of this methodology and finally resulted in the formation of sulfur-containing carbonylated products in good yields.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c04151

Authors: Ren-Guan Miao, Yuanrui Wang, Zhi-Peng Bao, Xiao-Feng Wu

Institutions: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Leibniz Institute for Catalysis, Dalian National Laboratory for Clean Energy

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Chinese Academy of Sciences, National Key Research and Development Program of China