Construction of sulfonated spiro[5,5]trienones from sulfur dioxide via iron-catalyzed dearomative spirocyclization of biaryls

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

---

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

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

---

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

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

---

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

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

---

Iminyl radical initiated sulfonylation of alkenes with rongalite under photoredox conditions

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

---

Photoinduced Radical Cascade Cyclization: A Metal-Free Approach to Access Difluoroalkylated Dioxodibenzothiazepines

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

---

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

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

---

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

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

---

Photochemical difluoromethylation of alkynes: synthesis of CF₂H-substituted seven-membered dioxodibenzothiazepines and dibenzazepines

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

---

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

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

---