C(sp3)–H Functionalization Enabled by Hydrogen Atom Transfer with Tertiary Cyclopropyl Radicals DOI

Synfacts, Journal Year: 2023, Volume and Issue: 19(09), P. 0888 - 0888

Published: Aug. 16, 2023

Key words C(sp3)–H functionalization - cyclopropyl radicals heteroarenes hydrogen atom transfer iron catalysis

Language: Английский

Photocatalytic Cyclization Cascades by Radical Relay toward Pyrrolo[1,2-a]indoles: Synthesis, Mechanism, and Application DOI

Chen He,

Qi Wang,

Xiaoyang Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3509 - 3524

Published: Feb. 16, 2024

A photocatalytic annulation cascade of unactivated N-alkene-linked indoles with Langlois' reagent by a radical relay is developed at room temperature under blue LED irradiation. The reaction afforded series tri/difluoromethylated pyrrolo[1,2-a]indoles in moderate to good yields. DFT study suggests that the ascribed rhodamine 6G-induced cyclization involving vinyl addition-radical and hydrogen-atom-abstraction (HAA) processes, interestingly, are applied as fluorescent dyes into fluorescence spectrum live-cell imaging. This paper represents an initial example on cascades HAA process.

Language: Английский

Citations

9

Structural Design of Single‐Atom Catalysts for Enhancing Petrochemical Catalytic Reaction Process DOI
Min Li,

Guangxun Sun,

Zhidong Wang

et al.

Advanced Materials, Journal Year: 2024, Volume and Issue: 36(25)

Published: March 18, 2024

Abstract Petroleum, as the “lifeblood” of industrial development, is important energy source and raw material. The selective transformation petroleum into high‐end chemicals great significance, but still exists enormous challenges. Single‐atom catalysts (SACs) with 100% atom utilization homogeneous active sites, promise a broad application in petrochemical processes. Herein, research systematically summarizes recent progress SACs catalytic reaction, proposes role structural design enhancing performance, elucidates reaction mechanisms conversion processes, reveals high activity origins at atomic scale. Finally, key challenges are summarized an outlook on design, identification appropriate artificial intelligence technology provided for achieving scale‐up process.

Language: Английский

Citations

7

Photocatalytic Multisite Functionalization of Unactivated Terminal Alkenes by Merging Polar Cycloaddition and Radical Ring‐Opening Process DOI
Haidong Liu, Yipeng Wang, Hui Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(41)

Published: July 18, 2024

Abstract Although highly appealing for rapid access of molecular complexity, multi‐functionalization alkenes that allows incorporation more than two functional groups remains a prominent challenge. Herein, we report novel strategy merges dipolar cycloaddition with photoredox promoted radical ring‐opening remote C(sp 3 )−H functionalization, thus enabling smooth 1,2,5‐trifunctionalization unactivated alkenes. A regioselective [3+2] anchors reaction trigger onto alkene substrates. The subsequent halogen atom transfer (XAT) selectively initiates process, which is followed by series 1,5‐hydrogen (1,5‐HAT) and intermolecular fluorine (FAT) events. With this method, site‐selective introduction three different accomplished broad spectrum valuable β‐hydroxyl‐ϵ‐fluoro‐nitrile products are synthesized from readily available terminal

Language: Английский

Citations

3

Stereoselective synthesis of tetra- and tri-substituted alkenyl nitriles via aminative ring-opening of cyclopropenes with iron-aminyl radical DOI Creative Commons
Qian Wang,

Jin-Kai Cheng,

Sheng Tang

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 3, 2025

Language: Английский

Citations

0

Synthesis of chiral difluoromethyl cyclopropanes through desymmetric difluoromethylation of cyclopropenes enabled by enantioselective copper catalysis DOI

Decai Ding,

Su Chen, Lingfeng Yin

et al.

Nature Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

Language: Английский

Citations

0

Electrochemical C–H silylation of azauracils with hydrosilanes DOI
Zhihua Zhang, Jingfang Wang, Changsheng Qin

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 583, P. 115218 - 115218

Published: May 24, 2025

Language: Английский

Citations

0

Overcoming Radical Stability Order via DABCO-Triggered Desulfurization: Visible-Light-Promoted 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate DOI
Xinyu Liu,

Jia‐Lin Fang,

Weidong Rao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 474 - 483

Published: Dec. 14, 2023

A radical 1,2,4-trifunctional reaction of thiosulfonate to unactivated olefin is achieved by a migration strategy under mild conditions. In this reaction, the more unstable primary free radicals are in situ generated after heteroaryl groups presence DABCO. This trifunctionalization olefins involves two C–S bond formations and one C–C formation.

Language: Английский

Citations

5

Sulfonyl Group-Induced Remote C(sp3)–N Bond Construction through Hydrogen Atom Transfer DOI
Haotian Li,

Xiancheng Qiu,

Xu Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(49), P. 8814 - 8818

Published: Dec. 6, 2023

This work demonstrates sulfonyl group-induced remote C(sp3)–N bond construction using a strategy of merging aryl radical-mediated halogen atom transfer and intramolecularly regioselective hydrogen (HAT). A plethora aliphatic sulfones, sulfonamides, sulfonates are amenable undergo C(sp3)–H amination by utilizing an iron salt at room temperature. protocol involves iodine transfer, HAT process enabled alkyl radical adjacent to group, mediated diazonium salt.

Language: Английский

Citations

4

Intramolecular Hydrogen Atom Transfer from Unactivated C(sp3)−H Bond to Alkyl Radical DOI
Huiying Liu,

Qihao Jin,

Xinxin Wu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(8)

Published: Jan. 20, 2024

Abstract Regioselective C( sp 3 )−H bond functionalization in atom‐ and step‐economic mode has long been recognized as a prominent challenging task due to its application late‐stage modification of complex skeletons, natural products drugs. As complement transition metal‐catalyzed C−H activation carbene/nitrene insertion reactions, hydrogen atom transfer (HAT) emerges versatile tool for showcases significant distinctive superiority terms selectivity trend substrate scope. Intramolecular HAT processes initiated by nitrogen‐ oxygen‐centered radicals, aryl vinyl have already well developed the past century. In contrast, development alkyl radical‐mediated reactions lagged behind, although generation methods corresponding radicals under mild conditions gained rapid growth. Especially, selective efficient from unactivated radical is highly their comparable BDEs polarity. This Concept highlights recent advance regioselective ubiquitous bonds enabled intramolecular H‐atom radicals.

Language: Английский

Citations

1

Remote Functionalization of Inert C(sp3)–H Bonds via Dual Catalysis Driven by Alkene Hydrofluoroalkylation Using Industrial Feedstocks DOI
Yan He,

Kang‐Jie Bian,

Peng Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(39), P. 8278 - 8283

Published: Sept. 19, 2024

We have developed a dual-catalytic system capable of site-selective azidation inert C(sp

Language: Английский

Citations

1