A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid

• DOI: 10.1038/ncomms15913
• Publication Date: 2017-06-26T09:51:57Z
• Authors: Keith G. Andrews; Radmila Faizova; Ross M. Denton
• Keywords: Trifluoroacetic acid; Primary (astronomy); Fluorine; Functional group

Abstract Amines are a fundamentally important class of biologically active compounds and the ability to manipulate their physicochemical properties through introduction fluorine is paramount importance in medicinal chemistry. Current synthesis methods for construction fluorinated amines rely on air moisture sensitive reagents that require special handling or harsh reductants limit functionality. Here we report practical, catalyst-free, reductive trifluoroethylation reactions free exhibiting remarkable functional group tolerance. The proceed conventional glassware without rigorous exclusion either oxygen, use trifluoroacetic acid as stable inexpensive source. new provide access wide range medicinally relevant functionalized tertiary β -fluoroalkylamine cores, direct secondary via three-component coupling primary amines, aldehydes acid. A reduction situ -generated silyl ester species proposed account selectivity observed.