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Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation.

ABSTRACT: Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C-H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.

SUBMITTER: Wang D

PROVIDER: S-EPMC7540508 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation.

Wang Dong D Carlton C Grace CG Tayu Masanori M McDouall Joseph J W JJW Perry Gregory J P GJP Procter David J DJ

Angewandte Chemie (International ed. in English) 20200715 37

Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C-H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction ...[more]

PMID: 32463942

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