ol2c03268_si_001.pdf (3.54 MB)
Ru-Catalyzed Hydrogen Atom Transfer/C–F Bond Cleavage of Difluoroalkyl Diazos with Hantzsch Ester via a Photocatalytic Radical Process
journal contributionposted on 2022-10-26, 11:03 authored by Qian Wang, Jiang Liu, Haibo Mei, Romana Pajkert, Mira Kessler, Gerd-Volker Röschenthaler, Jianlin Han
A Ru-catalyzed reaction of difluoroalkyl diazo compounds with Hantzsch ester under visible light to achieve the formation of α-fluorovinylphosphonates via a radical process has been developed. Mechanistic experiments and density functional theory calculations reveal that the generation of a carbon radical is directly through the hydrogen atom transfer (HAT) by Hantzsch ester. This system represents the first example of generation of carbon radicals from diazo compounds via Hantzsch-ester-assisted HAT and also demonstrates a new radical-involved pathway for the difluoroalkyl diazo compounds.
hydrogen atom transferdifluoroalkyl diazo compoundsphotocatalytic radical processhantzsch ester viaradical processhantzsch esterfluorovinylphosphonates viadifluoroalkyl diazosnew radicalcarbon radicalvisible lightsystem representsmechanistic experimentsinvolved pathwayfirst examplecatalyzed reactioncarbon radicalsalso demonstrates