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

Photoredox-Catalyzed Alkene Acylesterification with Acyloxime Esters via C–C and Tertiary C–O Bond Formation DOI

Youkang Zhou,

Ruiying Zhao, Mingyou Hu

et al.

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

Published: Jan. 7, 2025

We describe an efficient acyl esterification method for alkenes utilizing acyloxime esters as bifunctional reagents featuring radical acylation and congested C–O bond formation. This approach is characterized by mild photoredox conditions, high step atom economy, a broad substrate scope, excellent regioselectivity. A variety of valuable α-acyl hindered alcohol esters, including those obtained via gram-scale synthesis late-stage functionalization pharmaceutical molecules, were presented, demonstrating its synthetic potential practicability.

Language: Английский

Citations

3
Photoredox-Catalyzed Alkylamination of Alkenes via Oxidative Radical-Polar Crossover and Site-Selective 1,5-Hydrogen Atom Transfer DOI
Tianle Huang, Jianghong Liu,

Zhen-Ye Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6847 - 6852

Published: Aug. 7, 2024

We reported the visible-light-mediated photoredox-catalyzed oxidative radical-polar crossover and 1,5-hydrogen atom transfer combined site-selective remote C(sp

Language: Английский

Citations

4
Visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes to access α, β-unsaturated ketones DOI

Xun Yang,

Yuxuan Xiao, Ying Yin

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A general method for accessing α,β-unsaturated ketones through visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes has been developed.

Language: Английский

Citations

0
Direct Synthesis of 2-Hydroxytrifluoroethylacetophenones via Organophotoredox-Mediated Net-Neutral Radical/Polar Crossover DOI Creative Commons
Albert Gallego‐Gamo, Pau Sarró, Yingmin Ji

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11682 - 11692

Published: Aug. 1, 2024

Alkene difunctionalization is a very attractive tool in synthetic organic chemistry. Herein, we disclose an operationally and practically simple method to access 2-hydroxytrifluoroethylacetophenones from styrene derivatives via photoredox catalysis. This light-mediated transformation promotes the generation of 1-hydroxy-2,2,2-trifluoroethyl carbon-centered radical as key synthon, which undergoes Giese addition with styrenes followed by Kornblum oxidation process. The presented not only mild cost-effective, but also utilizes photocatalyst DMSO oxidant. Experimental investigations support operative mechanism net-neutral radical/polar crossover.

Language: Английский

Citations

3
Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles DOI

Keyuan Zhang,

Qi Jiang,

Chonglong He

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7971 - 7975

Published: Sept. 11, 2024

We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of broad spectrum highly substituted methylenecarbocycles but also introduces new mechanistic pathway with aryl group migration, surpassing conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

Language: Английский

Citations

3
Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/smiles rearrangement cascade DOI

Chonglong He,

Yulong Wang, Quanxin Li

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110253 - 110253

Published: July 1, 2024

Language: Английский

Citations

2
Decatungstate-Photocatalyzed Transformations of 2-Bromo-3,3,3-trifluoropropene for Selective Synthesis of Z/E-β-CF3-Enones DOI

Xiao-Ya Yuan,

Zhimin Lü,

Xianqiang Huang

et al.

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

Published: Dec. 2, 2024

Condition-controlled switchable and divergent transformations of cost-effective 2-bromo-3,3,3-trifluoropropene (BTP) aldehydes were realized using a decatungstate (TBADT)-photocatalyzed strategy. The hydroacylated products, i.e., β,β-Br,CF

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