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

Atroposelective [4+1] Annulation for the Synthesis of Isotopic Isoindolinones Bearing both Central and Axial Chirality DOI Creative Commons

Jun Gu,

Lihong Zhang,

Hongfeng Zhuang

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Isotopically chiral molecules have drawn much attention due to their practical applications in drug discovery. However, existing studies this area are mainly limited centrally and H/D exchange. Herein, we report a phosphoric acid-catalyzed atroposelective [4+1] annulation of ketoaldehydes 1H-indol-1-amines. By means strategy, series D- 18O-labeled atropisomers featuring both central axial chiralities synthesized with high enantioselectivities diastereoselectivities good excellent isotopic incorporation. Experimental density functional theory suggest that the reaction involves sequential condensation, cyclization isomerization cascade, which second step is enantio-determining process.

Language: Английский

Citations

1
Visible-light-induced dual catalysis for divergent reduction of nitro compounds with CO2 radical anion DOI
Pei Xu,

Tian-Zi Hao,

Zhitao Liu

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110899 - 110899

Published: Jan. 1, 2025

Language: Английский

Citations

0
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-Induced Arylcarboxylation of Activated Alkenes with Aryl Halides and Oxalate Enabled by Electron Donor–Acceptor Complex Formation DOI
Long Yin, Zhitao Liu,

Pei Xu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 29, 2025

Simultaneous construction of two new C-C bonds in the alkene substrates regioselectively is significantly challenging. Herein, we report an unprecedented regioselective arylcarboxylation strategy activated alkenes with readily available aryl halides and tetrabutylammonium oxalate as reductant C1 source under visible-light-induced conditions. The reaction proceeds smoothly to access various carboxylic acids absence any catalysts, additives, metal promoters, or pre-established CO2 atmosphere. electron donor-acceptor (EDA) complex formed between stoichiometric amounts trigger single-electron reduction relay process after irradiation visible light. situ generated oxalic radical anion species undergoes homolysis bond releases potent source, respectively, facilitate reductive carboxylation.

Language: Английский

Citations

0
Photoinduced Radical Approach for Desulfurative Alkylation of Cysteine Derivatives to Make Unnatural Amino Acids DOI
Pei Xu, Yiqin Liu,

Hui-Xian Jiang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 4, 2024

Unnatural amino acids (UAAs) are highly valuable molecules in organic synthesis, pharmaceutical sciences, and material science. Herein, we present a photocatalytic radical approach for desulfurative alkylation of cysteine derivatives with arenethiol as the hydrogen atom transfer catalyst making UAAs peptides. The formate salt, acting donor, situ generates reductive CO

Language: Английский

Citations

2
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

2