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Photocatalytic α‐Oxyamination of Stable Enolates, Silyl Enol Ethers, and 2‐Oxoalkane Phosphonic Esters
Author(s) -
Schroll Peter,
König Burkhard
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403433
Subject(s) - chemistry , enol , silylation , photocatalysis , deprotonation , photochemistry , medicinal chemistry , phosphine , yield (engineering) , silyl enol ether , organic chemistry , polymer chemistry , catalysis , ion , materials science , metallurgy
Abstract Fast α‐oxyamination of stable enolates, silyl enol ethers, and in situ deprotonated dialkyl 2‐oxoalkane phosphonates and diphenyl‐2‐oxoalkyl phosphine oxides was performed in the presence of [Ru(bpy) 3 ] 2+ (bpy = 2,2′‐bipyridyl) as a photocatalyst, 2,2,6,6‐tetramethylpiperidine nitroxide (TEMPO), and visible light. The key step was the light‐induced one‐electron oxidation of TEMPO into the 2,2,6,6‐tetramethylpiperidine‐1‐oxoammonium ion, which was nucleophilically attacked to yield α‐functionalized carbonyl compounds. The reaction time was significantly reduced by the use of the microreactor flow technique.