Metal-Free Synthesis of α‑Tertiary Amino Acid Derivatives via Photoinduced Cross-Coupling DOI
Hisashi Yamamoto, Abhijit Paul

Synfacts, Journal Year: 2024, Volume and Issue: 20(03), P. 0325 - 0325

Published: Feb. 14, 2024

Key words α-tertiary amino acids - cross-dehydrogenative coupling metal- and photocatalyst-free single electron transfer hydrogen atom

Language: Английский

Transition metal-free C(sp3)–H selenation of β-ketosulfones DOI

Dilshat Abdukerem,

Hui Chen,

Zechuan Mao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(10), P. 2075 - 2080

Published: Jan. 1, 2024

Direct C(sp 3 )-H selenation, which is most atom economical, remains a formidable challenge, and only few examples have been reported to date. In this article, we introduce the transition metal-free selenation with β-ketosulfones diselenides as material source.

Language: Английский

Citations

4

Photocatalytic site-selective radical C(sp3)–H aminoalkylation, alkylation and arylation of silanes DOI

Xingyi He,

Yizhi Zhang, Shanshan Liu

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Language: Английский

Citations

4

N-Trifluoroethoxy Benzotriazolium Triflate: A Readily Available Reagent for Direct Radical Trifluoroethoxylation of Alkenes DOI
Mingxi Chen, Yu Lu, Yiwen Shen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9586 - 9591

Published: Oct. 29, 2024

Herein, we describe the development and application of a novel benzotriazole-based reagent toward radical trifluoroethoxylation. Various alkene classes, including styrene derivatives, enol carbonates, allyl silanes, are viable reaction partners in this transformation, yielding diverse trifluoroethoxylated products. Furthermore, method is readily applicable for late-stage modification natural product drugs molecules. Mechanistic computational studies suggest intermediacy an OCH2CF3 generated under photocatalytic conditions.

Language: Английский

Citations

4

HI-Catalyzed Intermolecular Hydroarylation of Alkenyl Alcohols with Indole Nucleophiles to Access C3-Benzylated Indole Derivatives DOI
Boyuan Zhang, Yang Cui, Xiao-Long Yuan

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134699 - 134699

Published: May 1, 2025

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

Advances and developments in transition metal-free benzylic C(sp3)–H activation/functionalization reactions DOI Creative Commons
Fatemeh Doraghi,

Shahab Kermaninia,

Elika Salehi Ghalehsefid

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(19), P. 14691 - 14716

Published: Jan. 1, 2025

Transition metal-free benzylic C(sp 3 )–H activation is a direct strategy for forming C–C and C–X bonds. This review highlights C–H activation/annulation or activation/functionalization of toluenes using non-metal catalysts promoters.

Language: Английский

Citations

0

Dearomative difunctionalization of arenes via highly selective radical relay reactions DOI
Ning Lei, Qian Zhang, Tao Pan

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4654 - 4662

Published: Jan. 1, 2024

Dearomatization of arenes emerges as a reliable strategy for crafting intricate 3D polycyclic frameworks.

Language: Английский

Citations

1

Synergistic Copper‐Aminocatalysis for Direct Tertiary α‐Alkylation of Ketones with Electron‐Deficient Alkanes DOI Creative Commons

Qi‐Chao Shan,

You‐Wei Wu,

Mu‐Xiang Chen

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(31)

Published: June 17, 2024

Abstract In this study, a novel approach for the tertiary α‐alkylation of ketones using alkanes with electron‐deficient C─H bonds is presented, employing synergistic catalytic system combining inexpensive copper salts aminocatalysis. This methodology addresses limitations traditional alkylation methods, such as need strong metallic bases, regioselectivity issues, and risk over alkylation, by providing high reactivity chemoselectivity without necessity pre‐functionalized substrates. The dual strategy enables direct functionalization C(sp 3 )─H bonds, demonstrating remarkable selectivity in presence conventional that are adjacent to heteroatoms or π systems, which typically susceptible single‐electron transfer processes. findings contribute advancement techniques, offering practical efficient route construction )─C(sp ) paving way further developments synthesis complex organic molecules.

Language: Английский

Citations

1

Catalyst-Free Ring Opening of Azlactones in Water Microdroplets† DOI
Kumar Naveen,

Vishesh Singh Rawat,

Rahul Verma

et al.

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

Published: Jan. 1, 2024

A catalyst-free method was developed for the ring opening of azlactones (also known as oxazolones) in water microdroplets.

Language: Английский

Citations

1

Dearomative Difunctionalization of Arenes via Highly Selective Radical Relay Reactions DOI Creative Commons
Ke Zheng, Ning Lei, Qian Zhang

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 24, 2024

Abstract Dearomatization of arenes emerges as a reliable strategy for crafting intricate 3D polycyclic frameworks. Nonetheless, the development an efficient method dearomatization across diverse remains formidable challenge, particularly in case unactivated benzene. In this study, we present facile dearomative difunctionalization approach through highly selective radical relay reaction. The reaction operates under mild conditions, devoid metals, photocatalysts, and additives. This exhibits broad substrate scope exceptional functional group tolerance, successfully transforming various aromatics, including inert naphthalene benzene rings, indoles, pyrroles, benzofuran, thiophene. Bioactivity assessments reveal significant inhibitory effect synthesized complex frameworks on HCT 116 cancer cells, with subsequent mouse experiments providing compelling evidence its feasibility.

Language: Английский

Citations

0