Remote trifluoromethylthiolation of alcohols under visible light

TETRAHEDRON

卷:76

Article

Barday, Manuel¹  Blieck, Remi¹  Ruyet, Louise¹  Besset, Tatiana² 

[1] Normandie Univ, CNRS, UNIROUEN, INSA Rouen,COBRA,UMR 6014, F-76000 Rouen, France

[2] UMR6014 COBRA, 1 Rue Tesniere 76821, Mont St Aignan, France

关键词: Trifluoromethylthiolation;    Fluorine chemistry;    Visible light;    Remote position;    C(sp(3))-H bond functionalization;   

DOI  :  10.1016/j.tet.2020.131153

来源: Elsevier

【 摘 要 】

An unprecedented remote and regioselective trifluoromethylthiolation reaction of alcohols was developed. Under mild conditions, a panel of free-alcohols was selectively functionalized with TolSO(2)SCF(3) reagent as the SCF 3 source in the presence of hypervalent iodide (PIDA) under blue light irradiation. This approach offered an operationally simple tool for the construction of a challenging C(sp(3))-SCF3 bond at the delta-position of an alcohol by C(sp(3))-H bond functionalization. Initial mechanistic studies suggested a radical pathway. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

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