Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction

doi:10.6023/cjoc202110018

Abstract

The decarboxylative carbonylation of α-amino acids was carried out with N-benzoyl succinimide as the carbonylation reagent under the synergistic catalysis of fluorescent dye/nickel catalysts. In this reaction, 16 kinds of α-amino ketone-containing derivatives were synthesized with good yields (up to 78%), and the light conversion efficiency was up to 3.25×10^–1 mmol/(kW•h). In addition, the possible mechanism of the photocatalytic reaction was proposed: α-amino carboxylic acid was catalyzed by visible light to form α-amino alkyl radicals, which entered the nickel catalytic cycle and produced α-amino ketone target compound via oxidation addition and reduction elimination process. The reactions could generate a variety of α-amino ketones with broad substrate scope under mild conditions and might have widespread use in synthesis of α-amino ketone-containing drug molecules and peptide modifications.

Key words: photocatalysis, nickel catalysis, single electron transfer, decarboxylative coupling reaction

Cite this article

Weiguo Yu, Lingna Wang, Xiaocong Yu, Shuping Luo. Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1216-1223.

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Entry	Photocatalyst	Yield^b/% of 3a
1	4CzIPN	53
2	4DPAIPN	24
3	4CzIPA	15
4	5CzBN	n.r.^c
5	3CzClIPN	n.r.^c
6	3DPAIPN	n.r.^c

Entry	Photocatalyst	Yield^b/% of 3a
1	4CzIPN	53
2	4DPAIPN	24
3	4CzIPA	15
4	5CzBN	n.r.^c
5	3CzClIPN	n.r.^c
6	3DPAIPN	n.r.^c

Entry	Solvent	Yield^b/% of 3a
1	DMAc	53
2	DMF	12
3	DMSO	18
4	THF	n.r.^c
5	CH₃CN	n.r.^c
6	PhCH₃	16
7	1,4-Dioxane	n.r.^c

Entry	Solvent	Yield^b/% of 3a
1	DMAc	53
2	DMF	12
3	DMSO	18
4	THF	n.r.^c
5	CH₃CN	n.r.^c
6	PhCH₃	16
7	1,4-Dioxane	n.r.^c

Entry	Base	Yield^b/% of 3a
1	Cs₂CO₃	53
2	K₂HPO₄	17
3	DIPEA	n.r.^c
4	K₂CO₃	32
5	Et₃N	n.r. ^c
6	Pyridine	n.r. ^c

荧光染料和镍协同催化的脱羧羰基化反应