Mild defluorinative N-acrylation of amines with (trifluoromethyl)alkenes: synthesis of α-arylacrylamides DOI
Yuqi Li,

Rongbin Peng,

Zhaolong Ma

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

A practical and efficient method to access α-arylacrylamides via the N -acrylation of amines with (trifluoromethyl)alkenes cleavage three C(sp 3 )–F bonds is presented.

Language: Английский

Photoredox-Catalyzed Defluorinative Carboxylation of gem-Difluorostyrenes with Formate Salt DOI
Chao Sun, Quan Zhou, Chuan‐Ying Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 883 - 888

Published: Jan. 22, 2024

Herein, we present a transition-metal-free, easy handling protocol for regioselective carboxylation of gem-difluorostyrenes with sodium formate as the C1 source. 30 examples α-fluoracrylates were obtained in yields to 80% under these conditions. A defluorinative monofluorovinyl intermediate and consecutive photoinduced electron transfer mechanism proposed after investigation.

Language: Английский

Citations

26
Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines DOI
M Kellis,

Ming-Yao Tang,

Tong Qian

et al.

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

Published: Feb. 26, 2025

A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, (NH4)2CO3 through the cleavage five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this features mild conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification complex molecules, scalability, versatile synthetic transformations resulting heterocyclic compounds.

Language: Английский

Citations

1
Stereoselective hydrodefluorination of CF3-substituted alkenes and gem-difluoroalkenes by H− DOI
Dachang Bai, Xin Li, Fen Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1388 - 1394

Published: Jan. 1, 2024

Zn-catalyzed stereoselective hydrodefluorination of CF 3 -substituted alkenes, gem -difluoroalkenes and polyfluoroarenes by hydride ion addition has been realized through controlled C(sp )–F and/or 2 bonds cleavage.

Language: Английский

Citations

7
Formate and CO2 Enable Reductive Carboxylation of Imines: Synthesis of Unnatural α-Amino Acids DOI
Pei Xu, Wenwen Liu,

Tian-Zi Hao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 9750 - 9754

Published: June 28, 2024

Herein, a photocatalytic umpolung strategy for reductive carboxylation of imines the synthesis α-amino acids was disclosed. Carbon dioxide radical anion (CO

Language: Английский

Citations

6
Photocatalytic deuterocarboxylation of alkynes with oxalate DOI Creative Commons

Pei Xu,

Hao-Qiang Jiang,

Hui Xu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(32), P. 13041 - 13048

Published: Jan. 1, 2024

Herein, a catalytic photoredox-neutral strategy for alkyne deuterocarboxylation with tetrabutylammonium oxalate as the carbonyl source and D

Language: Английский

Citations

5
Visible-Light-Promoted Cascade Carboxylation/Arylation of Unactivated Alkenes with CO2 for the Synthesis of Carboxylated Indole-Fused Heterocycles DOI

Yang Han,

Qi Yang,

Yang Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6341 - 6346

Published: July 18, 2024

Described here is a visible-light-promoted cascade carboxylation/arylation of indole-tethered unactivated alkenes with CO

Language: Английский

Citations

4
Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate DOI

Chen-Wei Xu,

Si-Yi Yan,

Hui Xu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 11967 - 11973

Published: July 26, 2024

Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source reductant well promoter is described. Neither pre-established CO2 atmosphere nor external electron donors are required TBAO crucial transformation. Various primary, secondary, tertiary could be smoothly converted to corresponding aryl acetic acids, which core structures diverse pharmaceutical drugs.

Language: Английский

Citations

4
Formate Salts: The Rediscovery of Their Radical Reaction under Light Irradiation Opens New Avenues in Organic Synthesis DOI

Qing Shen,

Kun Cao,

Xiaoqing Wen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4274 - 4293

Published: Aug. 17, 2024

Abstract Formates are abundantly available and inexpensive commodity chemical, widely used in laboratory industrial organic synthesis. promising hydrogen carrier green C1 source, have also been a subject of research as SET reductants recent years. Compared to the toxic flammable gas carbon monoxide, which serves formates easier handle, store, transport, more environmentally friendly. Therefore, studies radical reactions, formate is not only an ideal source carbonyl, great significance synthesize carboxyl compounds with various structures, but reductant for editing molecules either scientific or production. The activation conversion formate, reductant, very challenging hot field

Language: Английский

Citations

4
Mild [3 + 3] Annulation of (Trifluoromethyl)alkenes with Thioureas Enabled by Chemoselective Defluorinative Amination: Synthesis of 6-Fluoro-3,4-dihydropyrimidine-2(1H)-thiones DOI

Rongbin Peng,

Chuanle Zhu

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1538 - 1548

Published: Jan. 21, 2025

The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1H)-thiones in high yields, features transition-metal free, mild conditions, efficient, operationally simple and gram-scalable, tolerates diverse useful functional groups.

Language: Английский

Citations

0
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