Photocatalytic three-component radical cascade: a general route to heterocyclic-substituted alkyl sulfones DOI
Jian-Qiang Chen, Nana Liu, Qian Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(19), P. 5316 - 5321

Published: Jan. 1, 2021

A photoredox-catalyzed three-component radical cascade reaction of β,γ-unsaturated oximes/hydrazones, the sulfur dioxide surrogate DABCO·(SO 2 ) and alkenes under mild conditions is developed.

Language: Английский

Construction of sulfonated spiro[5,5]trienones from sulfur dioxide via iron-catalyzed dearomative spirocyclization of biaryls DOI
Fu‐Sheng He,

Lingjing Su,

Feiyan Yu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(7), P. 1937 - 1942

Published: Jan. 1, 2022

An iron-catalyzed dearomative spirocyclization of biaryl ynones with sodium metabisulfite and cycloketone oxime esters is developed for the construction sulfonated spiro[5,5]trienones.

Language: Английский

Citations

29

Photo- or Electrochemical Cyclization of Dienes with Diselenides to Access Seleno-Benzo[b]azepines DOI

Pengpeng Tan,

Liwang Lu,

Shilong Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7245 - 7255

Published: May 23, 2023

A cascade selenylation/cyclization of dienes with diselenides has been realized under visible-light irradiation or electrolysis conditions. Employing O2 electricity as a "green" oxidant, this protocol provides green and efficient method for an array biologically important seleno-benzo[b]azepine derivatives in moderate to good yields. The direct sunlight gram-scale reaction render the approach practical attractive.

Language: Английский

Citations

18

Base-catalyzed stereoselective thiosulfonylation of ynones for the facile synthesis of thio-functionalized vinyl sulfones DOI

Jinyun Luo,

Muze Lin,

Dengpeng Xia

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1224 - 1229

Published: Jan. 1, 2023

Brønsted base catalyzed thiosulfonylation and trifluoromethylthiosulfonylation of ynones produced thio-functionalized vinyl sulfones in high yields with excellent E -selectivity.

Language: Английский

Citations

17

A visible-light photoredox-catalyzed four-component reaction for the construction of sulfone-containing quinoxalin-2(1H)-ones DOI

Yufen Lv,

Jinyun Luo,

Muze Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(19), P. 5403 - 5409

Published: Jan. 1, 2021

A visible-light photoredox-catalyzed four component reaction of quinoxalin-2(1 H )-ones, alkenes, aryldiazonium, and sodium metabisulfite leading to sulfone-containing )-ones has been developed.

Language: Английский

Citations

38

Iminyl radical initiated sulfonylation of alkenes with rongalite under photoredox conditions DOI
Fu‐Sheng He, Man Zhang, Mengke Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(14), P. 3746 - 3751

Published: Jan. 1, 2021

A photoredox-catalyzed reaction of oximes, rongalite and electrophiles is accomplished, affording pyrrole-substituted aliphatic sulfones or sulfonamides in moderate to good yields.

Language: Английский

Citations

37

Photoinduced Radical Cascade Cyclization: A Metal-Free Approach to Access Difluoroalkylated Dioxodibenzothiazepines DOI
Qian Xiao,

Maojian Lu,

Ying‐Lan Deng

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(23), P. 9303 - 9308

Published: Nov. 22, 2021

A simple and mild photoredox catalytic approach to access difluoroalkylated dioxodibenzothiazepines in high regioselectivity via radical cascade cyclization has been described herein. In contrast previous methods, this strategy does not involve the use of transition-metal catalysts avoids potential disadvantages inevitable toxicity tedious removal process metal catalysts. The commercially available inexpensive CF2 precursors, wide substrate scope, reaction conditions demonstrate practicability approach.

Language: Английский

Citations

36

The synthesis of seven- and eight-membered rings by radical strategies DOI

Xuan-Chi Yu,

Cancan Zhang,

Ling‐Tao Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4757 - 4781

Published: Jan. 1, 2022

Radical strategies for preparation of seven- or eight-membered rings.

Language: Английский

Citations

27

Metal-free synthesis of sulfonylated indolo[2,1-a]isoquinolines from sulfur dioxide DOI

Binyan Qin,

Shaoxin Huang,

Jian-Qiang Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(13), P. 3521 - 3526

Published: Jan. 1, 2022

Access to sulfonylated indolo[2,1- a ]isoquinolines through an efficient three-component reaction of 2-aryl- N -acryloyl indoles, sulfur dioxide and aryldiazonium tetrafluoroborates is developed.

Language: Английский

Citations

25

Photochemical difluoromethylation of alkynes: synthesis of CF2H-substituted seven-membered dioxodibenzothiazepines and dibenzazepines DOI
Xiaoyu Chen, Yang Geng, Bo Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 1968 - 1974

Published: Jan. 1, 2023

A general and efficient photochemical strategy for difluoromethylation/radical cascade cyclization of alkynes with sodium difluoromethylsulfinate (NaSO 2 CF H) has been disclosed.

Language: Английский

Citations

15

Photoinduced Alkylsulfonylation and Cyanoalkylsulfonylation of Morita–Baylis–Hillman Adducts via Multicomponent Insertion of Sulfur Dioxide DOI

Song Zhi-jie,

Yu Bao,

Yun-Jia Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4877 - 4887

Published: March 8, 2024

General and convenient visible-light-promoted alkylsulfonylation cyanoalkylsulfonylation of MBH adducts have been developed through the multicomponent insertion sulfur dioxide, enabling assembly two C–S bonds to generate structurally diverse allylic alkylsulfones (43 examples in total). The reaction with potassium alkyltrifluoroborates 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct afforded sulfones generally good yields. Notably, addition N,N,N′,N′-tetramethylethylenediamine as a base into photocatalytic system led yielding an alkyl sulfonyl unit cyano group-anchored trisubstituted alkenes by utilizing cycloketone oxime esters C-radical precursors. Both these reactions constructed bonds, all desired products were obtained moderate excellent yields complete stereospecificity.

Language: Английский

Citations

6