Trifluoromethylthiolation of Diazo Compounds through Copper Carbene Migratory Insertion

Trifluoromethylthiolation of Diazo Compounds through Copper Carbene Migratory Insertion

A strategy to introduce the SCF3 group through the CuI‐promoted reaction of diazo compounds with the nucleophilic AgSCF3 trifluoromethylthiolation reagent was developed. Various diazo compounds were smoothly converted under mild conditions to form the C(sp3)–SCF3 bond. Mechanistically, migratory ins...

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Veröffentlicht in:European journal of organic chemistry 2014-05, Vol.2014 (15), p.3093-3096
Hauptverfasser: Wang, Xi, Zhou, Yujing, Ji, Guojing, Wu, Guojiao, Li, Ming, Zhang, Yan, Wang, Jianbo
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Carbenes
Diazo compounds
Fluorine
Migratory insertion
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container_end_page 3096
container_issue 15
container_start_page 3093
container_title European journal of organic chemistry
container_volume 2014
creator Wang, Xi
Zhou, Yujing
Ji, Guojing
Wu, Guojiao
Li, Ming
Zhang, Yan
Wang, Jianbo
description A strategy to introduce the SCF3 group through the CuI‐promoted reaction of diazo compounds with the nucleophilic AgSCF3 trifluoromethylthiolation reagent was developed. Various diazo compounds were smoothly converted under mild conditions to form the C(sp3)–SCF3 bond. Mechanistically, migratory insertion of SCF3‐bearing Cu carbene intermediates is involved in this transformation. A strategy to introduce the SCF3 group through the CuI‐promoted reaction of diazo compounds with the nucleophilic AgSCF3 trifluoromethylthiolation reagent is developed. Various diazo compounds are smoothly converted under mild conditions to form the C(sp3)–SCF3 bond. Migratory insertion of SCF3‐bearing CuI carbene intermediates is proposed as the key step in this transformation.
doi_str_mv 10.1002/ejoc.201402105
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subjects Carbenes
Diazo compounds
Fluorine
Migratory insertion
title Trifluoromethylthiolation of Diazo Compounds through Copper Carbene Migratory Insertion
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