Access to cyclic gem-difluoroacyl scaffolds via electrochemical and visible light photocatalytic radical tandem cyclization of heteroaryl chlorodifluoromethyl ketones

Abstract

A variety of unprecedented scaffolds containing a difluoroacyl moiety were obtained in moderate to good yields, with excellent diastereoselectivity, via electrochemical or photochemical activation of difluoroacyl heteroaryles with a series of olefinic substrates.

An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor

“…26 This highlights the efficiency of electrochemistry and its complementarity compared to photoredox catalysis. 27 Furthermore, poorly soluble starting materials like 4-mercaptobenzoic acid (22) could also be converted using this protocol.…”

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…Médebielle and co-workers reported an electrochemical method to homolyze the C–Cl bond in chlorodifluoromethyl ketones, enabling the synthesis of heteroarene compounds containing difluoroacyl moieties. 717 …”

Methods for the Synthesis of α,α‐Difluoroketones

“…This process gave fused six‐membered difluoroketone systems such as 99 . Medibielle has reported a related cyclisation of CF 2 Cl ketones with electron‐rich alkenes, using either Ru(bpy) 3 Cl 2 photoredox activation or electrochemical activation giving similar six‐membered products 100 . The electrochemical process proved to be faster and more amenable to scale‐up than photoredox, but both gave similar yields in general.…”