Visible-Light-Driven Carboxylative 1,2-Difunctionalization of C═C Bonds with Tetrabutylammonium Oxalate DOI Creative Commons

Sai Wang,

Pei Xu, Zhitao Liu

et al.

ACS Central Science, Journal Year: 2024, Volume and Issue: 11(1), P. 46 - 56

Published: Nov. 15, 2024

Herein, we report a visible-light-induced charge-transfer-complex-enabled dicarboxylation and deuterocarboxylation of C═C bonds with oxalate as masked CO2 source under catalyst-free conditions. In this reaction, disclosed the first example that tetrabutylammonium could be able to aggregate aryl substrates via π–cation interactions form charge transfer complexes, which subsequently triggers single electron from oxalic dianion ammonium countercation irradiation 450 nm bule LEDs, releasing radical anions. Diverse alkenes, dienes, trienes, indoles, including challenging trisubstituted olefins, underwent anti-Markovnikov high selectivity access valuable 1,2- 1,4-dicarboxylic acids well indoline-derived diacids β-deuterocarboxylic mild The in situ generated CO2•– molecules anions both add bond without assistance any photocatalyst or additives, made reaction sustainable, clean, efficient.

Language: Английский

Synthetic application of oxalate salts for visible-light-induced radical transformations DOI

Hui-Xian Jiang,

Zhitao Liu, Pei Xu

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111224 - 111224

Published: April 1, 2025

Language: Английский

Citations

0
Visible-Light-Driven Carboxylative 1,2-Difunctionalization of C═C Bonds with Tetrabutylammonium Oxalate DOI Creative Commons

Sai Wang,

Pei Xu, Zhitao Liu

et al.

ACS Central Science, Journal Year: 2024, Volume and Issue: 11(1), P. 46 - 56

Published: Nov. 15, 2024

Herein, we report a visible-light-induced charge-transfer-complex-enabled dicarboxylation and deuterocarboxylation of C═C bonds with oxalate as masked CO2 source under catalyst-free conditions. In this reaction, disclosed the first example that tetrabutylammonium could be able to aggregate aryl substrates via π–cation interactions form charge transfer complexes, which subsequently triggers single electron from oxalic dianion ammonium countercation irradiation 450 nm bule LEDs, releasing radical anions. Diverse alkenes, dienes, trienes, indoles, including challenging trisubstituted olefins, underwent anti-Markovnikov high selectivity access valuable 1,2- 1,4-dicarboxylic acids well indoline-derived diacids β-deuterocarboxylic mild The in situ generated CO2•– molecules anions both add bond without assistance any photocatalyst or additives, made reaction sustainable, clean, efficient.

Language: Английский

Citations

1