A photoinduced transient activating strategy for late-stage chemoselective C(sp³)-H trifluoromethylation of azines.

ABSTRACT: The direct functionalization of C(sp³)-H bonds is an ultimately ideal synthetic strategy with high atom economy and step efficiency. However, the direct trifluoromethylation of electron-deficient heteroaryl adjacent C(sp³)-H bonds remains a formidable challenge. We have described a transient activating strategy involving a Tf-shift process and π-π stacking interaction for catalyst-free direct benzylic C(sp³)-H trifluoromethylation of azines, such as pyridine, pyrimidine, quinoline, dihydropyridinone, tetrahydroisoquinoline and tetrahydroquinazoline, with an air-stable crystalline imidazolium sulfonate reagent IMDN-Tf. This bench-stable cationic reagent offers a scalable and practical protocol for the late-stage modification of drug molecules with high site

SUBMITTER: Huang M 

PROVIDER: S-EPMC9533475 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature