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

Sai Wang,

Pei Xu, Zhitao Liu

и другие.

ACS Central Science, Год журнала: 2024, Номер 11(1), С. 46 - 56

Опубликована: Ноя. 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.

Язык: Английский

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

Tian-Zi Hao,

Zhitao Liu

и другие.

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 110899 - 110899

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
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

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

0
Synthetic application of oxalate salts for visible-light-induced radical transformations DOI

Hui-Xian Jiang,

Zhitao Liu, Pei Xu

и другие.

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 111224 - 111224

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

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

Yiqin Liu,

Hui-Xian Jiang

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 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

Язык: Английский

Процитировано

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

Sai Wang,

Pei Xu, Zhitao Liu

и другие.

ACS Central Science, Год журнала: 2024, Номер 11(1), С. 46 - 56

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

1