Copper‐Catalyzed Radical Difluoromethylation‐Peroxidation of Alkenes: Synthesis of β‐Difluoromethyl Peroxides DOI
Fan Liu, Leiyang Lv, Yangyang Ma

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(9)

Published: July 25, 2022

Abstract A convenient and efficient copper‐catalyzed three‐component difluoromethylation‐peroxidation of alkenes with commercially‐available sodium difluoromethanesulfinate tert ‐butyl hydroperoxide has been developed. This protocol enables the synthesis a variety β ‐difluoromethyl peroxides under mild conditions. Versatile synthetic transformations difluoromethyl have also explored.

Language: Английский

Recent advances in combining photo- and N-heterocyclic carbene catalysis DOI Creative Commons
Xiaochen Wang,

Senhui Wu,

Rongxin Yang

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(46), P. 13367 - 13383

Published: Jan. 1, 2023

This review summarizes recent advances in combining photo- and N-heterocyclic carbene catalysis, as well provides an outlook on future opportunities challenges.

Language: Английский

Citations

43

Recent advances in N-heterocyclic carbene (NHC)-catalyzed fluorination and fluoroalkylation DOI

Zefeng Jin,

Fuxiang Zhang, Xiao Xiao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2112 - 2133

Published: Jan. 1, 2024

Organofluorine compounds are of high value. NHC-catalyzed fluorination and fluoroalkylation have served as powerful versatile vehicles for accessing the related organofluorines. This review focuses on recent developments in this area.

Language: Английский

Citations

25

Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds DOI
Jiaqiong Sun, Lihong V. Wang, Guangfan Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4488 - 4515

Published: Jan. 1, 2023

This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on mechanistic insights these transformations.

Language: Английский

Citations

31

Synthesis of β-Thiolated-α-arylated Ketones Enabled by Photoredox and N-Heterocyclic Carbene-Catalyzed Radical Relay of Alkenes with Disulfides and Aldehydes DOI

Hai‐Wu Du,

Ming‐Shang Liu, Wei Shu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(30), P. 5519 - 5524

Published: July 21, 2022

β-Thiolated-α-arylated ketones are perversive in bioactive molecules and serve as potential bidentate ligands for catalysis. Herein, a straightforward protocol to access β-thiolated from aldehydes, alkenes, disulfides enabled by the combination of photocatalysis N-heterocyclic carbene catalysis is reported. The sequential radical addition alkenes subsequent radical–radical coupling cascade process simultaneously forge C–S C–C bonds. mild conditions allow relay with broad functional group tolerance.

Language: Английский

Citations

34

Radical acylation: concepts, synthetic applications and directions DOI
Yue Zhang, Yili Zhang, Jian Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1056 - 1085

Published: Jan. 1, 2023

In this tutorial, reaction scopes, limitations and mechanisms of radical acylations are summarized discussed according to types catalytic systems.

Language: Английский

Citations

21

Recent Advances in Visible Light‐Mediated Radical Fluoro‐alkylation, ‐alkoxylation, ‐alkylthiolation, ‐alkylselenolation, and ‐alkylamination DOI Creative Commons
Daniel Lin, Matthew Coe, Vinayak Krishnamurti

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(9)

Published: May 22, 2023

Abstract In the last few years, many reagents and protocols have been developed to allow for efficient fluorofunctionalization of a diverse set scaffolds ranging from alkanes, alkenes, alkynes, (hetero)arenes. The concomitant rise organofluorine chemistry visible light‐mediated synthesis synergistically expanded fields mutually benefitted developments in both fields. this context, light driven formations radicals containing fluorine major focus discovery new bioactive compounds. This review details recent advances progress made fluoroalkylation heteroatom centered radical generation.

Language: Английский

Citations

20

Radical Acylation of Alkenes by NHC‐Organocatalysis DOI Open Access
Qian Tang, Ding Du, Jian Gao

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(48)

Published: Oct. 11, 2023

Abstract N ‐Heterocyclic carbene (NHC) catalyzed radical‐radical reactions have been proven to be powerful strategies for assembling ketyl‐containing compounds via single electron transfer (SET) pathway under either thermal conditions or photoredox conditions. In this context, acylation of alkenes radical relay NHC‐organocatalysis has also opened a new window the difunctionalization construct valuable molecules in organic synthesis. review, advances and progress were summarized according different ways generation key NHC‐bound ketyl‐type radicals. Furthermore, reaction scopes, limitations mechanisms discussed based on types catalytic systems. Conclusions perspectives put forward at end.

Language: Английский

Citations

17

Visible-light-promoted desulfonylative radical difluoroalkylation between difluoroenol silyl ethers and difluoroalkyl sulfones to construct functionalized aryltetrafluoroethane derivatives DOI

Miaomiao Mu,

Xiaolei Zhu, Jinshan Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1444 - 1449

Published: Jan. 1, 2024

A visible-light-promoted desulfonylative radical difluoroalkylation between difluoroenol silyl ethers and difluoroalkyl sulfones has been developed.

Language: Английский

Citations

8

Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Polycyclic Imidazoles DOI Creative Commons
S.J. Lin, Yuanyuan Deng,

Hanxun Zhong

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(26), P. 28129 - 28143

Published: June 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Language: Английский

Citations

5

Organocatalytic Three-Component Acyldifluoromethylation of Vinylarenes via N-Heterocyclic Carbene-Catalyzed Radical Relay DOI

Kun She,

Liang Feng,

Shichao Tian

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(26), P. 4840 - 4844

Published: June 27, 2022

We herein describe an N-hetercyclic carbene-catalyzed three-component acyldifluoromethylation of vinylarenes, aldehydes, and NaSO2CF2H. This organocatalytic approach provides a practical route for the synthesis pharmaceutically relevant α-aryl-β-difluormethyl ketones without need transition metals or photocatalysts. The late-stage drug analogues was also demonstrated. reaction design employs NaSO2CF2H as source CF2H radical in presence oxidant relay.

Language: Английский

Citations

20