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Csp³-H Trifluoromethylation of Unactivated Aliphatic Systems.

ABSTRACT: A straightforward method for the undirected trifluoromethylation of unactivated methylene units was developed. The reaction proceeds in aqueous acetonitrile with Grushin's reagent, bpyCu(CF₃)₃, under broad-spectrum white-light irradiation. The trifluoromethylation tolerates a wide range of functional groups including ketones, esters, nitriles, amides, alcohols, and carboxylic acids. The C-H cleavage step is performed via intermolecular H atom abstraction, and the selectivities across a range of methylene units are reported. Mechanistic studies offer a general reaction coordinate for the overall transformation.

SUBMITTER: He J

PROVIDER: S-EPMC9199362 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Csp3-H Trifluoromethylation of Unactivated Aliphatic Systems.

He Jiachen J Nguyen Truong N TN Guo Shuo S Cook Silas P SP

Organic letters 20210114 3

A straightforward method for the undirected trifluoromethylation of unactivated methylene units was developed. The reaction proceeds in aqueous acetonitrile with Grushin's reagent, bpyCu(CF3)3, under broad-spectrum white-light irradiation. The trifluoromethylation tolerates a wide range of functional groups including ketones, esters, nitriles, amides, alcohols, and carboxylic acids. The C-H cleavage step is performed via intermolecular H atom abstraction, and the selectivit ...[more]

PMID: 33443442

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