Metal-free photocatalyzed homo- and cross-dimerizations of α-hydroxyl ketones via dual C(sp3)–H functionalization: synthesis of 2,3-dihydroxyl-1,4-butanediones
Zhouying Wang,
Enrong Tang,
Quanquan Zhou
et al.
Abstract:The dimerization reactions of α-hydroxy ketones in the α-carbon site have been realized by visible light photocatalysis in the fashion of both homo- and cross coupling, leading to the synthesis...
“…10 Benefiting from the dramatic advances of visible light induced transformation, 11 our group has recently reported the first metal-free photocatalytic homo- and cross-dimerization of α-hydroxy ketones via a radical process. 12 While Ritter reactions involving carbocation generation via alcohol dehydroxylation or benzyl C–H functionalization have been reported, using α-hydroxy ketones as precursors for Ritter-type amidation remains unknown. On the other hand, catalytic transformation of ubiquitous C–H and C–OH bonds into C–N bonds represents a valuable strategy for fabricating nitrogen-containing compounds.…”
Visible light-induced, transition metal-free oxidative dehydroxylation and C–H amidation of α-hydroxy ketones involving Ritter-type amidation has been developed, leading to the selective synthesis of α,α-diamido- and α-monoamido ketones.
“…10 Benefiting from the dramatic advances of visible light induced transformation, 11 our group has recently reported the first metal-free photocatalytic homo- and cross-dimerization of α-hydroxy ketones via a radical process. 12 While Ritter reactions involving carbocation generation via alcohol dehydroxylation or benzyl C–H functionalization have been reported, using α-hydroxy ketones as precursors for Ritter-type amidation remains unknown. On the other hand, catalytic transformation of ubiquitous C–H and C–OH bonds into C–N bonds represents a valuable strategy for fabricating nitrogen-containing compounds.…”
Visible light-induced, transition metal-free oxidative dehydroxylation and C–H amidation of α-hydroxy ketones involving Ritter-type amidation has been developed, leading to the selective synthesis of α,α-diamido- and α-monoamido ketones.
Reported herein is a new photocatalytic annulation for the synthesis of 2,3,4,6-tetrasubstituted pyridines with enaminones and N,N,N′,N′-tetramethyl ethylenediamine (TMEDA). The photocatalytic reactions take place without requiring a transition metal reagent and provide products with broad scope. The methyl in TMEDA acts as the carbon source in pyridine ring construction, and BrCF 2 CO 2 Et plays the role of the terminal oxidant for free radical quenching.
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