Visible-Light Photoredox-Catalyzed Carbon/Carboxylation of Alkenes with Malonates and CO2

doi:10.6023/cjoc202406038

Abstract

A photoredox-catalyzed cascade carbon/carboxylation of activated alkenes with malonates acetals and CO₂ has been achieved, leading to a range of functionalized 1,1,3-tricarboxylates in good efficiency under mild reaction conditions. This reaction provides a facile and sustainable method for the synthesis of tricarboxylates by using CO₂ as the carboxylic source.

Key words: carbon dioxide, carboxylation, alkene difunctionalization, visible-light catalyzed

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Aolong Zhang, Han Yang, Peidong Cheng, Yang Yao, Song Sun. Visible-Light Photoredox-Catalyzed Carbon/Carboxylation of Alkenes with Malonates and CO₂[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3159-3168.

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Entry	Catalyst	Base	Solvent	3aa yield^b/%
1	PC1	Na₂CO₃	DMSO	24
2	PC2, PC3	Na₂CO₃	DMSO	<5
3	PC4	Na₂CO₃	DMSO	90
4	PC4	Cs₂CO₃	DMSO	62
5	PC4	K₂CO₃	DMSO	71
6	PC4	K₃PO₄	DMSO	65
7	PC4	Et₃N	DMSO	N.R.
8	PC4	Na₂CO₃	DMF	56
9	PC4	Na₂CO₃	DMAc	17
10	PC4	Na₂CO₃	1,4-Dioxane	N.R.
11	PC4	Na₂CO₃	MeCN	N.R.
12	PC4	Na₂CO₃	DMSO	63^c, 70^d, 66^e
13	PC4	Na₂CO₃	DMSO	85^f, 84^g, 77^h, 81ⁱ
14	PC4	Na₂CO₃	DMSO	71^j, 75^k
15^l	PC4	Na₂CO₃	DMSO	0
16^m	PC4	Na₂CO₃	DMSO	91

Entry	Catalyst	Base	Solvent	3aa yield^b/%
1	PC1	Na₂CO₃	DMSO	24
2	PC2, PC3	Na₂CO₃	DMSO	<5
3	PC4	Na₂CO₃	DMSO	90
4	PC4	Cs₂CO₃	DMSO	62
5	PC4	K₂CO₃	DMSO	71
6	PC4	K₃PO₄	DMSO	65
7	PC4	Et₃N	DMSO	N.R.
8	PC4	Na₂CO₃	DMF	56
9	PC4	Na₂CO₃	DMAc	17
10	PC4	Na₂CO₃	1,4-Dioxane	N.R.
11	PC4	Na₂CO₃	MeCN	N.R.
12	PC4	Na₂CO₃	DMSO	63^c, 70^d, 66^e
13	PC4	Na₂CO₃	DMSO	85^f, 84^g, 77^h, 81ⁱ
14	PC4	Na₂CO₃	DMSO	71^j, 75^k
15^l	PC4	Na₂CO₃	DMSO	0
16^m	PC4	Na₂CO₃	DMSO	91

可见光促进烯烃与丙二酸酯、CO₂的碳-羧化反应研究

Visible-Light Photoredox-Catalyzed Carbon/Carboxylation of Alkenes with Malonates and CO₂

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可见光促进烯烃与丙二酸酯、CO2的碳-羧化反应研究