Photoredox Catalyzed Reductive Trifluoromethylation of Imines via radical umpolung strategy DOI

Hrishikesh Paul,

Dibyangshu Das,

SK Ariyan

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A photocatalyzed radical-umpolung strategy is developed to synthesize trifluoromethylated α-unnatural amino acids and amines. This method involves the migration of an N-centred radical through aromatic framework construct C–CF 3 bond.

Language: Английский

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
Photoredox/Palladium-Catalyzed Reduction Alkylation of Imines and Ammonium Salts via Dual C–N Bond Cleavage DOI
Tao Ju, Zhi‐Hao Wang,

Ai-Ling Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 16, 2025

Here, we report a photoredox/palladium-catalyzed reduction alkylation of imines and ammonium salts via dual C-N cleavage. This reaction proceeds under mild, green, operationally simple conditions, offering broad scope secondary amine compounds with alpha quaternary carbon. Mechanistic studies indicate that the α-amino carbanion, generated by successive single-electron transfer process, is key intermediate in photoredox/palladium catalysis.

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
Harnessing (Phenylsulfonyl)difluoromethyl Sulfonium Salt: A Radical Approach to Photoredox-Catalyzed Functionalization of Unsaturated Compounds with the PhSO2CF2 Group DOI Creative Commons
Sourav Roy, Tatiana Besset

JACS Au, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 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
EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate DOI

Min‐Hang Zhou,

Jun Jiang, Wei‐Min He

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110446 - 110446

Published: Sept. 1, 2024

Language: Английский

Citations

2
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
EDA-Enabled Three-Component Polarity-Crossover Cyclization: Modular Installation of Fully Substituted γ-Lactams DOI

Jingqi Yan,

Zhilin Liu, Kai Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9598 - 9603

Published: Oct. 28, 2024

A photoinduced three-component radical addition-aminalization cascade was accomplished, enabling rapid assembly of a wide range densely functionalized γ-lactams. Key to this transformation is the electron-donor-acceptor (EDA) generation enamine and in situ trapping an iminium intermediate with bromodifluoroacetamide. This rationally designed protocol fully takes advantage polarity crossover (enamine-iminium) process, providing modular previously inaccessible scaffolds. The reaction proceeds under mild conditions excellent regio- diastereoselectivity, which amenable structurally varied substrates pharmaceuticals.

Language: Английский

Citations

1
Dual NHC/HAT‐Promoted Esterification to Access α‐Aryl Glycines DOI Creative Commons
Matthew J. McGill, Adam X. Wayment,

Cullen R. Schull

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 31, 2024

Abstract α‐Aryl glycines are among the most important carbonyl compounds, particularly as nonproteinogenic α‐amino acids present in many pharmacophores. As such, strategies have been developed to access this motif, but direct carboxylation methods remain underdeveloped. Herein, we employ a dual NHC/HAT catalysis strategy 2‐azaallyl radicals, which subsequently couple with situ‐ generated ester azolium radical intermediates. Base‐mediated collapse of ensuing tetrahedral intermediate liberates NHC catalyst and benzophenone‐protected aryl glycine. This methodology was employed esterify variety aryl‐substituted glycine derivatives, well allylic benzylic sites. Mechanistic studies reveal that process operates under both oxidative reductive quenching cycles, while preliminary experiments employing chiral Lewis acid additive demonstrate modest enantioselectivity.

Language: Английский

Citations

1