Electrochemical trifluoroalkylation/annulation for the synthesis of CF3-functionalized tetrahydroquinolines and dihydroquinolinones DOI

Hao-Zeng Wu,

Zhong-Shan Teng,

Yu-Xin Ke

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8579 - 8583

Published: Jan. 1, 2023

Tuning the electronic structure of protecting groups on nitrogen atom substrates has emerged as an effective strategy to achieve tandem trifluoromethylation/C(sp2)-H annulation using Langlois' reagent CF3 source for electrochemical synthesis functionalized tetrahydroquinolines and dihydroquinolinones.

Language: Английский

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications DOI
Mingzhu Lu, Jeffrey Goh, Manikantha Maraswami

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(24), P. 17479 - 17646

Published: Oct. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Language: Английский

Citations

155
Harnessing photocatalytic and electrochemical approaches for C–H bond trifluoromethylation and fluoroalkylation DOI
Ranjay Shaw, Naveen Sihag, Hemaang Bhartiya

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 954 - 1014

Published: Dec. 14, 2023

The review summarises various photo- and electrochemical strategies for trifluoromethylation fluoroalkylation of different C(sp 3 )–H, 2 C(sp)–H bonds in several classes organic molecules.

Language: Английский

Citations

14
Electrochemical oxidative regio- and stereo-selective thio(seleno)cyanation of enamides and mechanistic insights DOI

Qingyun Gu,

Zhenfeng Cheng,

Xing Xiong

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(17), P. 6556 - 6561

Published: Jan. 1, 2022

An electrochemical oxidative thio(seleno)cyanation of enamides to synthesize various ( E )-β-thio(seleno)cyanated enamide compounds is reported herein.

Language: Английский

Citations

17
Transition metal-free electrochemical fluorotrifluoromethylation of Styrenes DOI
Yi Lu, Zhirui Liu, Chao Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1283 - 1288

Published: Jan. 1, 2023

An environmentally friendly electrochemical fluorotrifluoromethylation of styrenes is developed using CF 3 SO 2 Na and Et N·3HF as the F-containing donor reagents. This synthetic strategy features step economy sustainability.

Language: Английский

Citations

10
Recent Advances in the Electrochemical Functionalization of Isocyanides DOI

Qingyun Gu,

Zhenfeng Cheng,

Xiaodong Qiu

et al.

The Chemical Record, Journal Year: 2022, Volume and Issue: 23(1)

Published: Sept. 20, 2022

Abstract Isocyanides are well‐known as efficient CO surrogates and C1 synthons in modern organic synthesis. Although tremendous efforts have been devoted to fully exploiting the reactivity of isocyanides, these transformations primarily limited by their utilization stoichiometric toxic chemical oxidants. With recent resurgence electrochemistry, which has considerably laid dormant over past several decades, electrolysis identified a green powerful tool enrich structural diversity solely utilizing electric current clean inherently safe redox equivalents In this regard, unique isocyanides studied numerous electrochemical transformations. This review comprehensively highlights most relevant progress strategies towards functionalization up until June 2022, with focus on reaction outcomes mechanisms.

Language: Английский

Citations

15
Electrochemical trifluoroalkylation/annulation for the synthesis of CF3-functionalized tetrahydroquinolines and dihydroquinolinones DOI

Hao-Zeng Wu,

Zhong-Shan Teng,

Yu-Xin Ke

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8579 - 8583

Published: Jan. 1, 2023

Tuning the electronic structure of protecting groups on nitrogen atom substrates has emerged as an effective strategy to achieve tandem trifluoromethylation/C(sp2)-H annulation using Langlois' reagent CF3 source for electrochemical synthesis functionalized tetrahydroquinolines and dihydroquinolinones.

Language: Английский

Citations

2