Visible-Light-Driven Alkene Dicarboxylation with Formate and CO2 Under Mild Conditions DOI Creative Commons
Fulin Zhang, Xiaoyang Wu, Panpan Gao

et al.

Published: Aug. 3, 2023

The low-cost formate salt was used as the reductant and part of carboxyl source in a visible-light-driven dicarboxylation diverse alkenes, including simple styrenes. highly competing hydrocarboxylation side reaction successfully overridden. Good yields products were obtained under mild reactions at ambient temperature pressure CO2. dual role may stimu-late discovery range new transformations friendly conditions.

Language: Английский

Recent Advances in Reactions Involving Carbon Dioxide Radical Anion DOI
Wei Xiao, Jun Zhang, Jie Wu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(24), P. 15991 - 16011

Published: Nov. 28, 2023

Carbon dioxide radical anion (CO2•–) is a highly reactive nucleophilic species that has recently emerged in organic chemistry as strong single electron donor (reductant) and reactant for the synthesis of carboxylic acids. In general, CO2•– can be generated by either direct reduction CO2 or HAT formate salts. Achievements reactions involving have been witnessed recent years. This Review summarizes advances highlighting some challenges identifying potential areas improvement, which may offer inspiration future studies.

Language: Английский

Citations

55
Visible-light-driven alkene dicarboxylation with formate and CO2 under mild conditions DOI Creative Commons
Fulin Zhang, Xiaoyang Wu, Panpan Gao

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 6178 - 6183

Published: Jan. 1, 2024

Low-cost formate salt was used as the reductant and part of carboxyl source in a visible-light-driven dicarboxylation diverse alkenes, including simple styrenes. The highly competing hydrocarboxylation side reaction successfully overridden. Good yields products were obtained under mild conditions at ambient temperature pressure CO

Language: Английский

Citations

13
Visible-Light-Induced Defluorinative α-C(sp3)–H Alkylation for the Synthesis of gem-Difluoroallylated α-Trifluoromethylamines DOI

Bingran Chen,

Qinlin Chen,

Yang Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9124 - 9129

Published: Nov. 17, 2023

Herein, we describe a novel and efficient photoredox catalytic Cα radical addition/defluoroalkylation coupling reaction between α-trifluoromethyl alkenes N-trifluoroethyl hydroxylamine. A series of gem-difluoroallylated α-trifluoromethylamines were synthesized by the addition enabled 1,2-H shift in situ-generated radical. Notably, this protocol is distinguished its mild conditions, easy operation, excellent functional group tolerability.

Language: Английский

Citations

19
Visible-Light Mediated, Dual-Catalysis Enabled Allylic Difluoroalkylation via Halogen Atom Transfer DOI

Shivani Arora,

P. K. Katiyar,

Tripti Singh

et al.

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

Published: April 1, 2025

A visible-light-mediated protocol employing a halogen atom transfer strategy (XAT) has been developed for the synthesis of homoallylic difluorinated compounds. Employing dual-catalysis reactivity manifold, which includes cobaloxime catalyst, reaction occurs without exogenous oxidant and under mild conditions. The applicability unactivated olefins, wide variety halogenated precursors, access to diverse family difluoromethylated molecular architectures are highlights this method.

Language: Английский

Citations

0
Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds DOI

Jia‐Wei Liu,

Shiyu Li, Jun Xu

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(8)

Published: Dec. 28, 2023

Abstract The selective C−F bonds functionalization in available trifluoromethyl compounds is an economic route for obtaining high‐value organic fluorine compounds. However, due to the high dissociation energy group, strength of bond decreases continuously during defluorination, posing a challenge modifying such molecules without over‐conversion. Over past few years, there has been significant progress developing efficient methods constructing difluoromethylene unit, using approaches as radical chemistry, photochemistry, electrochemistry, and organometallic chemistry. These involve difluorocarbon radicals, cations, anions, carbenes intermediates. In this review, we summarized recent five years research achievements field single cleavage aromatic carbonyl gain diverse difluoromethylene‐containing via different intermediate strategies.

Language: Английский

Citations

6
Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF3 tertiary alcohols DOI

Min-Ming Lu,

Ning Deng, Shiyu Li

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(15), P. 8694 - 8700

Published: Jan. 1, 2024

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes under an air atmosphere was developed to construct densely functionalized α-CF 3 tertiary alcohols.

Language: Английский

Citations

1
Visible Light Induced Selective Cleavage of Single C(sp3)-F Bond in Trifluoromethyl Groups Containing Compounds DOI
Fang Wang,

Qidi Wang,

Lei Wang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 163, P. 134155 - 134155

Published: July 16, 2024

Language: Английский

Citations

1
Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study DOI Open Access
Yoshihiko Yamamoto, Norihiko Goto, Takeshi Yasui

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

β-(Trifluoromethyl)styrenes are potentially useful building blocks for the synthesis of organofluorine compounds because their electron-deficient C=C double bonds can undergo diverse transformations. One most practical methods preparing β-(trifluoromethyl)styrenes is decarboxylative trifluoromethylation readily available cinnamic acid derivatives using Langlois reagent as a less expensive trifluoromethyl source. We revisited electrochemical to identify modified conditions that reduce loading without additional additives. The reaction mechanism was computationally investigated gain insight into dependence product yields on aryl terminal groups. synthetic utility obtained demonstrated by transformation 4-aryl-3-(trifluoromethyl)pyrrolidines.

Language: Английский

Citations

0
Visible-Light-Induced Markovnikov Hydroalkoxylation of α-Trifluoromethyl Alkenes with ortho-Diketones DOI

Qinlin Chen,

Rundong Fan,

Xuliang Deng

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

We report, for the first time, a visible-light-promoted Markovnikov hydroalkoxylation of α-trifluoromethyl alkenes with 1,2-diketones. This transformation proceeded smoothly in presence tertiary amine (Et

Language: Английский

Citations

0
Visible-Light-Driven Alkene Dicarboxylation with Formate and CO2 Under Mild Conditions DOI Creative Commons
Fulin Zhang, Xiaoyang Wu, Panpan Gao

et al.

Published: Aug. 2, 2023

The low-cost formate salt was used as the reductant and part of carboxyl source in a visible-light-driven dicarboxylation diverse alkenes, including simple styrenes. highly competing hydrocarboxylation side reaction successfully overridden. Good yields products were obtained under mild reactions at ambient temperature pressure CO2. dual role may stimu-late discovery range new transformations friendly conditions.

Language: Английский

Citations

1