Exploiting single-electron transfer in Lewis pairs for catalytic bond-forming reactions DOI Creative Commons
Yoshitaka Aramaki,

Naoki Imaizumi,

Mao Hotta

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(17), P. 4305 - 4311

Published: Jan. 1, 2020

Radical–ion pair generation from common Lewis pairs and its application to catalytic carbon–carbon bond formation.

Language: Английский

Recent advances in the sulfonylation of alkenes with the insertion of sulfur dioxide via radical reactions DOI
Guanyinsheng Qiu,

Lifang Lai,

Jiang Cheng

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(74), P. 10405 - 10414

Published: Jan. 1, 2018

Recent advances in the sulfonylation of alkenes via insertion sulfur dioxide are summarized. The surrogate DABCO·(SO2)2 or inorganic sulfites is used transformation through a radical process. Two strategies for with have been developed. In most cases, vicinal difunctionalization initiated by arylsulfonyl generated situ. Although efficient, asymmetric versions still challenging and less to be explored. It expected that will developed rapidly near future.

Language: Английский

Citations

209

Alkene 1,2‐Difunctionalization by Radical Alkenyl Migration DOI Creative Commons
Xinjun Tang, Armido Studer

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 57(3), P. 814 - 817

Published: Nov. 22, 2017

Abstract Transition‐metal‐free radical α‐perfluoroalkylation with the accompanying vicinal β‐alkenylation of unactivated alkenes is presented. These cascades proceed by means 1,4‐ or 1,5‐alkenyl migration electron catalysis on readily accessed allylic alcohols. The reactions comprise a regioselective perfluoroalkyl addition subsequent alkenyl and concomitant deprotonation to generate ketyl anion that sustains chain as single‐electron‐transfer reducing reagent.

Language: Английский

Citations

197

Recent advances in catalyst-free photochemical reactions via electron-donor-acceptor (EDA) complex process DOI

Yan‐Qin Yuan,

Swarup Majumder, Ming‐Hua Yang

et al.

Tetrahedron Letters, Journal Year: 2019, Volume and Issue: 61(8), P. 151506 - 151506

Published: Dec. 9, 2019

Language: Английский

Citations

197

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis DOI
Xue‐Qiang Chu, Danhua Ge,

Yan-Ying Cui

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(20), P. 12548 - 12680

Published: Aug. 13, 2021

As the "chemical chameleon", sulfonyl-containing compounds and their variants have been merged with various types of reactions for efficient construction diverse molecular architectures by taking advantage incredible reactive flexibility. Currently, involvement in radical transformations, which sulfonyl group typically acts as a leaving via selective C–S, N–S, O–S, S–S, Se–S bond cleavage/functionalization, has facilitated new formation strategies are complementary to classical two-electron cross-couplings organometallic or ionic intermediates. Considering great influence synthetic potential these novel avenues, we summarize recent advances this rapidly expanding area discussing reaction designs, substrate scopes, mechanistic studies, limitations, outlining state-of-the-art processes involved radical-mediated desulfonylation related transformations. With specific emphasis on applications, believe review will be useful medicinal organic chemists who interested chemistry particular.

Language: Английский

Citations

180

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes DOI Creative Commons

Zhonglie Yang,

Yutong Liu, Kun Cao

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 17, P. 771 - 799

Published: April 6, 2021

The reversible, weak ground-state aggregate formed by dipole–dipole interactions between an electron donor and acceptor is referred to as electron-donor–acceptor (EDA) complex. Generally, upon light irradiation, the EDA complex turns into excited state, causing transfer give radicals initiate subsequent reactions. Besides external energy source, reactions involving participation of complexes are mild, obviating transition metal catalysts or photosensitizers in majority cases line with theme green chemistry. This review discusses synthetic concerned well mechanisms that have been shown over past five years.

Language: Английский

Citations

130

Beyond classical sulfone chemistry: metal- and photocatalytic approaches for C–S bond functionalization of sulfones DOI Creative Commons
Javier Corpas, Shin‐Ho Kim‐Lee, Pablo Mauleón

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(15), P. 6774 - 6823

Published: Jan. 1, 2022

Sulfones are excellent candidates for the design of new C–C and C–X bond-forming reactions owing to easy activation C–S bonds. This review focuses on challenges recent opportunities catalytic functionalization sulfones.

Language: Английский

Citations

80

Recent Advances in Electron Donor‐Acceptor (EDA)‐Complex Reactions involving Quaternary Pyridinium Derivatives DOI

Barakha Saxena,

Roshan I. Patel,

Anuj Sharma

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(10), P. 1538 - 1564

Published: March 6, 2023

Abstract Quaternary pyridinium compounds are valuable intermediates in organic synthesis, which have gained immense popularity the synthetic community. The application of transition metal or photoredox catalysis transforming quaternary into various C−C and C−X bonds is well established. A majority these methods require high temperatures, expansive catalysts, delicate conditions for successful execution. On other hand, use metal‐free photocatalysis‐free strategies constructing using derivatives has been sought‐after. In this context, electron‐donor‐acceptor (EDA)‐complex reactions emerged as a state‐of‐the‐art methodology, do not any photocatalyst their EDA‐complex photochemistry takes advantage electron‐acceptor ability derivatives, can quickly generate radical precursor via deaminative process. These newly generated useful several transformations. We hereby, review, discuss an area major progress mediated involving with mechanism, substrate scope, limitations. magnified image

Language: Английский

Citations

44

China's flourishing synthetic organofluorine chemistry: innovations in the new millennium DOI Creative Commons
Qinghe Liu, Chuanfa Ni, Jinbo Hu

et al.

National Science Review, Journal Year: 2017, Volume and Issue: 4(3), P. 303 - 325

Published: May 1, 2017

Abstract The new millennium has witnessed the rapid development of synthetic organofluorine chemistry all over world, and chemists in China have made significant contributions this field. This review aims to provide a brief introduction China's primary innovations from 2000 early 2017, covering fluorination, fluoroalkylation, fluoromethylthiolation, fluoroolefination polyfluoroarylation, as well synthesis with fluorinated building blocks. Recent advances difluorocarbene carbon–fluorine bond activation are also discussed. As conclusion, ends some personal perspectives on future chemistry.

Language: Английский

Citations

159

Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay DOI
Liang Fu, Song Zhou, Xiaolong Wan

et al.

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(35), P. 10965 - 10969

Published: Aug. 22, 2018

A novel enantioselective copper-catalyzed trifluoromethylalkynylation of styrenes, proceeding through a radical relay process, is described herein, which affords structurally diverse CF3-containing propargylic compounds in good yield with excellent enantioselectivities under very mild conditions. In addition, the reaction features wide substrate scope and functional group tolerance. Moreover, trifluoromethylalkynylated products can be easily converted into synthetically useful chiral terminal alkynes, allenes, Z-alkenes, as well CF3-modified nonsteroidal anti-inflammatory drugs.

Language: Английский

Citations

154

α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration DOI Creative Commons
Xinjun Tang, Armido Studer

Chemical Science, Journal Year: 2017, Volume and Issue: 8(10), P. 6888 - 6892

Published: Jan. 1, 2017

Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented.

Language: Английский

Citations

141