Work

Csp3–H Trifluoromethylation of Unactivated Aliphatic Systems

Year: 2021

Type: article

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(CF 3 ) 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.0c03891

Authors: Jiachen He, Truong N. Nguyen, Shuo Guo, Silas P. Cook

Institutions: Indiana University Bloomington, Indiana University

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, Eli Lilly and Company, Indiana University, National Institute of General Medical Sciences

Award: Methods for the Functionalization of C-H Bonds