Trifluoromethylthiolation Carbonylation of Unactivated\nAlkenes via Distal Migration

Sulfur-containing\ncompounds represent a significant category of\norganic compounds, and the introduction of sulfur groups into organic\ncompounds can effectively enhance their biological activity and synthetic\ndiversity. Although a variety of difunctionalization reactions of\nalkenes based on sulfur radicals have been documented, significant\nchallenges remain in the carbonylative difunctionalization of unactivated\nalkenes by the addition of a sulfur radical. Herein, we present a\ntrifluoromethylthiolative carbonylation reaction of unactivated alkenes,\nwhich goes through the addition of a trifluoromethylthiol radical\nto unactivated alkenes and then carbonylation of the newly generated\ncarbon radical intermediate. A heterocyclic/aryl migration in the\npresence of carbon monoxide is crucial for the success of this methodology\nand finally resulted in the formation of sulfur-containing carbonylated\nproducts in good yields.

Publication Details

Journal
Figshare
Published
2024-11-20
DOI
https://doi.org/10.1021/acs.orglett.4c04151.s001
Primary Topic
Libraries and Information Services
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article
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article

Trifluoromethylthiolation Carbonylation of Unactivated\nAlkenes via Distal Migration

Figshare
Libraries and Information Services
article

Trifluoromethylthiolation Carbonylation of Unactivated\nAlkenes via Distal Migration

article en

Abstract

Sulfur-containing\ncompounds represent a significant category of\norganic compounds, and the introduction of sulfur groups into organic\ncompounds can effectively enhance their biological activity and synthetic\ndiversity. Although a variety of difunctionalization reactions of\nalkenes based on sulfur radicals have been documented, significant\nchallenges remain in the carbonylative difunctionalization of unactivated\nalkenes by the addition of a sulfur radical. Herein, we present a\ntrifluoromethylthiolative carbonylation reaction of unactivated alkenes,\nwhich goes through the addition of a trifluoromethylthiol radical\nto unactivated alkenes and then carbonylation of the newly generated\ncarbon radical intermediate. A heterocyclic/aryl migration in the\npresence of carbon monoxide is crucial for the success of this methodology\nand finally resulted in the formation of sulfur-containing carbonylated\nproducts in good yields.

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