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Trifluoromethylthiolation-arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling.

ABSTRACT: A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C-SCF₃ and C-C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF₃ group arise from different reagents. Our studies show that the reaction mechanism is similar to the Hooz multicomponent coupling. The process involves in situ generation of BAr₃, which reacts with a diazocarbonyl compound, and the reaction is terminated by an electrophilic SCF₃ transfer. The reaction can also be extended to fluorination based bifunctionalization which proceeds with somewhat lower yield than the analogous trifluoromethylthiolation reaction.

SUBMITTER: Lubcke M

PROVIDER: S-EPMC6571710 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Trifluoromethylthiolation-arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling.

Lübcke Marvin M Bezhan Dina D Szabó Kálmán J KJ

Chemical science 20190506 23

A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C-SCF3 and C-C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF3 group arise from different reagents. Our studies show that the reaction mechanism is similar to the Hooz multicomponent coupling. The process involves in situ generation of BAr3, which reacts with a diazocarbonyl compound, and the reacti ...[more]

PMID: 31360406

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