Thermo-induced decarboxylative α-C(sp³)–H fluoroalkylation of glycine derivatives with fluorinated peroxy esters

Abstract

A thermo-induced decarboxylative α-C(sp3)−H fluoroalkylation of glycine derivatives with fluorinated peroxy esters was described. This protocol features transition metal free, redox-neutral conditions, broad substrate scope and excellent functional group tolerance,...

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

“…As our continuous interest in C­(sp 3 )–H functionalization of peptides (Scheme d) , and fluorine chemistry, we herein describe a novel transformation that includes the organo-photoredox-catalyzed C­(sp 3 )–H difluoroallylation of glycine and glycine-containing peptides with α-trifluoromethyl alkenes through intermolecular α-amino carbanion addition (Scheme e), producing the structurally diverse β- gem -difluoroalkyl glycine derivatives in moderate to good yields. − …”

Metal-free, visible-light driven α-C(sp3)–H gem-difluoroallylation of glycine derivatives with trifluoromethyl alkenes and 1,3-enynes

“…16 Our group disclosed a metal free thermo-induced decarboxylative α-C(sp 3 )–H fluoroalkylation of glycine derivatives with the fluorinated peroxy esters. 17 In view of the importance of FAAs, we intend to develop the direct C–H fluoroalkylation of glycine derivatives with more easily available, stable, and easily operational difluoroalkylation reagents. As mentioned above, the trifluoromethyl alkenes are attractive synthons in the radical gem -difluoroallylations.…”

Iron-Catalyzed Alkoxyl Radical-Induced C–C Bond Cleavage/gem-Difluoroalkylation Cascade

“…3 In this regard, our group disclosed a new type of fluorinated peroxy ester, which enabled α-C(sp 3 )−H difluoroalkylation of glycine derivatives under conditions free of transition metals. 4 Compared with radical precursors, the difluoroalkylation reagents serving as radical acceptors are relatively rare.…”

“…For instance, functionalized difluoroalkyl halides [GFCF 2 X, where FG = CO 2 Et, CONHR, PO­(OEt) 2 , COAr, or SO 2 Ph] were commonly used as efficient radical precursors in various difluoroalkylation reactions . In this regard, our group disclosed a new type of fluorinated peroxy ester, which enabled α-C­(sp 3 )–H difluoroalkylation of glycine derivatives under conditions free of transition metals . Compared with radical precursors, the difluoroalkylation reagents serving as radical acceptors are relatively rare.…”