Work

Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines

Year: 2023

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N -dialkylhydrazones and trifluoromethylarenes (CF 3 -arenes). This method relies on selective C–F bond cleavage via reduction of the CF 3 -arene. We show that a diverse set of CF 3 -arenes and CF 3 -heteroarenes react smoothly with a range of aryl and alkyl hydrazones. The β-difluorobenzylic hydrazine product can be selectively cleaved to form the corresponding benzylic difluoroarylethylamines.

Source: Organic Letters

DOI: 10.1021/acs.orglett.3c00126

Authors: Cecilia M. Hendy, Cameron J. Pratt, Nathan T. Jui, Simon B. Blakey

Institution: Emory University

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences