Electrochemical Stereoselective Synthesis of (Z)‐Allyl Aryl Selenides and Sulfides from Baylis‐Hillman Acetates DOI
Li Sun,

Mengcan Xia,

Guorui Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1152 - 1157

Published: Jan. 9, 2024

Abstract This research presents a method for the oxidative selenylation and thiolylation of Morita‐Baylis‐Hillman adducts through constant‐current electrolysis in an undivided cell at room temperature. The reaction enables direct production trisubstituted ( Z )‐allyl aryl selenides sulfides with yields 27–98%. A wide variety different functionalities are well tolerated under these conditions. strategy could be carried out on gram scale several synthetic transformations were accomplished construction other allyl selenide derivatives. Control experiments mechanistic studies indicate radical or ionic addition pathway this electrochemical transformation.

Language: Английский

Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 450 - 470

Published: Nov. 3, 2023

Language: Английский

Citations

50
Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes DOI
Pei Qu,

You‐Qin Jiang,

Yong‐Hao Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7485 - 7507

Published: Jan. 1, 2023

The recent advances on the electrochemical selenofunctionalization of unsaturated C–C bonds were comprehensively summarized in this review.

Language: Английский

Citations

32
Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation DOI
Jianchao Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

Citations

30
Electrochemical oxidative radical cascade reactions for the synthesis of difluoromethylated benzoxazines DOI

Xiang Chen,

Jun Jiang, Xiaojun Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3898 - 3902

Published: Jan. 1, 2023

An efficient electrochemical synthesis of fluoroethylated benzoxazines via oxyfluoromethylation was developed. The broad applicability and general utility were tested highlighted by the substrate scope late-stage synthesis.

Language: Английский

Citations

25
Recent Advances in Electrochemical Cascade Cyclization Reactions DOI
Cai Zhang, Yunyun Liu,

Demao Chen

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2911 - 2925

Published: Feb. 20, 2023

Abstract This review highlights recent progress in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, such as pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-α]pyridines, imidazoles, etc. The works included herein are introduced two major sections heterocycle construction carbocycle reactions, covering reported from 2012 to 2022. 1 Introduction 2 Electrochemical Cascade Cyclization Synthesis Heterocycles 2.1 Pyridines, Quinolines, Phenanthridines, Cinnolines 2.2 1,4-Dihydroquinolines, Hexacyclic Sulfonamides, Thiazines 2.3 Hydroisoquinolinones Hydroquinolinones 2.4 Quinazolin-4(3H)-ones 2.5 4H-3,1-Benzoxazines 2.6 Oxindoles 2.7 Indolines Indoles 2.8 Imidazo[1,5-α]pyridines Imidazoles 2.9 Imidazolones, Imidazolidinones, Oxazolones, Oxazolidinones 2.10 Benzoxazoles, Oxazolines, Isoxazolines 2.11 Furans Dihydrofurans 2.12 Indolizines, Pyrazoles, Triazolium Inner Salts 2.13 Sulfonated Benzothiophenes, Thiazoles, Dihydrothiazoles, 1,3,4-Thiadiazoles 2.14 Lactones 3 Construction Carbocycles 3.1 Carbon Polycycles Spiroindenes 3.2 Difluoroacyl (Hetero)arenes Indenones 4 Conclusion

Language: Английский

Citations

23
Electrochemical oxidative selenocyclization of olefinic amides towards the synthesis of iminoisobenzofurans DOI
Hao Li, Fangling Lu, Jie Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(10), P. 2786 - 2791

Published: Jan. 1, 2022

We introduced an electrochemical oxidative radical cascade cyclization of olefinic amides and diselenides without a transition-metal catalyst external oxidant. This selenocyclization reaction provided facile method to construct C–Se C–O bonds in one step.

Language: Английский

Citations

38
Versatile electrooxidative amino- and oxyselenation of alkenes DOI
R. Wang,

Nana Zhang,

Yonghong Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3925 - 3930

Published: Jan. 1, 2023

We herein describe a methodology for the production of organoselenium compounds by electrocatalytic difunctionalisation alkenes.

Language: Английский

Citations

20
Electrochemical reductive cross-coupling of acyl chlorides and sulfinic acids towards the synthesis of thioesters DOI
Jie Xu, Fangling Lu,

Linghong Sun

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(19), P. 7350 - 7354

Published: Jan. 1, 2022

In this context, we used an electrochemical reduction method to obtain thiyl radicals from sulfinic acids. a simple undivided cell, various acyl chlorides and acids were compatible, generating 40 examples of the desired thioesters.

Language: Английский

Citations

26
Regioselective Photocatalytic Dialkylation/Cyclization Sequence of 3‐Aza‐1,5‐dienes: Access to 3,4‐Dialkylated 4‐Pyrrolin‐2‐ones DOI
Xiao Hu,

Minglin Tao,

Zhongxiao Ma

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(13), P. 2163 - 2168

Published: June 3, 2022

Abstract A visible‐light‐induced regioselective tandem enamido β‐C( sp 2 )−H alkylation/acrylamido alkylation/cyclizative alkenylation sequence of 3‐aza‐1,5‐dienes is presented. This protocol regiospecific, features a broad substrate scope, and provides direct access to 3,4‐dialkylated 4‐pyrrolin‐2‐ones from readily available N ‐alkenylacrylamides. It scalable gram scale, could be induced by natural sunlight. magnified image

Language: Английский

Citations

23
Electrochemical oxidative cascade cyclization of olefinic amides and alcohols leading to the synthesis of alkoxylated 4H-3,1-benzoxazines and indolines DOI

Wan‐Jie Wei,

Lei Zhan,

Caina Jiang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(3), P. 928 - 933

Published: Jan. 1, 2023

We have developed a mild and efficient electrochemical oxidative strategy to construct anticancer alkoxylated 4 H -3,1-benzoxazines indolines without the requirement for transition-metal catalyst an external oxidant.

Language: Английский

Citations

16