Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

Asymmetric sulfonylation with sulfur dioxide surrogates: a new access to enantiomerically enriched sulfones DOI
Jun Zhang, Peiqi Wang, Yanzhi Li

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(26), P. 3821 - 3826

Published: Jan. 1, 2023

In this highlight, we survey recent exciting advances in asymmetric sulfonylation by using sulfur dioxide surrogates, and discuss induction modes, reaction mechanisms, substrate scope opportunities for further studies.

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
Phenanthroline-Initiated Anti-selective Hydrosulfonylation of Unactivated Alkynes with Sulfonyl Chlorides DOI

Ci-Shuang Dong,

Wen‐Yan Tong,

Peng Ye

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(10), P. 6983 - 6993

Published: May 8, 2023

A simple and general method for anti-selective hydrosulfonylation of unactivated alkynes with sulfonyl chlorides in the presence a catalytic amount phenanthroline-based Lewis base (Me3Si)3SiH as hydrogen atom donor has been developed. The protocol proceeds efficiently under mild metal-free conditions, delivering diverse set (Z)-vinyl sulfones high stereoselectivity. Additionally, displays excellent functional-group compatibility can be applied to late-stage modifications complex drugs their derivatives. Experimental density functional theory studies unveiled that key transformation's success is employment base, which interacts form halogen-bond accelerates cleavage S–Cl bonds irradiation visible light.

Language: Английский

Citations

26
Visible‐Light Induced Fixation of SO2 into Organic Molecules with Polypyridine Chromium(III) Complexes DOI Creative Commons

Steven Sittel,

Arne C. Sell,

Kamil Hofmann

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(6)

Published: Jan. 23, 2023

Abstract Incorporation of sulfur dioxide into organic compounds is achieved by a photocatalytic approach using sensitizers made from earth‐abundant chromium(III) ions and visible light leading to sulfones sulfonamides. We employed three different [Cr(ddpd) 2 ] 3+ , [Cr(bpmp) [Cr(tpe) with long excited state lifetimes ground redox potentials as well varying stability under the reaction conditions (ddpd= N N’ ‐dimethyl‐ ’‐dipyridin‐2‐yl‐pyridine‐2,6‐diamine; bpmp=2,6‐bis(2‐pyridylmethyl)pyridine; tpe=1,1,1‐tris(pyrid‐2‐yl)ethane). Key steps catalytic cycles are identified electrochemical, luminescence quenching, photolysis, laser flash photolysis experiments delivering detailed picture challenges in these transformations. The reactivity reduced chromium complex was key property explain outcomes. Initial cage escape yield determinations revealed that desired photoreactions occur unusually high quantum efficiencies, whereas side reactions almost unproductive.

Language: Английский

Citations

24
Visible light-initiated manganese-catalyzed hydrosulfonylation of alkenes DOI
Chunmin Li,

Xin-Xin Dong,

Zhe Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 4122 - 4128

Published: Jan. 1, 2023

A visible light-initiated manganese-catalyzed radical hydrosulfonylation of a wide range structurally diverse alkenes using commercially available and relatively cheap sulfonyl chlorides as sources is described.

Language: Английский

Citations

24
Single-Electron-Transfer-Generated Aryl Sulfonyl Ammonium Salt: Metal-Free Photoredox-Catalyzed Modular Construction of Sulfonamides DOI
Fengying Yan, Qing Li,

Shanshan Fu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5227 - 5235

Published: March 21, 2024

Sulfonamides are prominently featured in organic synthesis and medicinal chemistry. Yet, a general synthetic platform for the modular construction of aryl sulfonamides remains elusive. Herein, metal-free photoredox-catalyzed three-component via an sulfonyl ammonium salt intermediate, which was generated situ SET event, has been established. A variety structurally diverse primary, secondary, tertiary were synthesized rapidly from abundant amines or sodium azide under mild conditions. Notably, primary aliphatic amine, challenging Cu-catalyzed protocols, worked well this approach. Moreover, fluoride can be accessed smoothly as well, using potassium hydrogen nucleophile. The potential utility conversion is demonstrated facile three bioactive drug compounds. Preliminary mechanistic studies have revealed that radical key intermediates mechanistically innovative methodology.

Language: Английский

Citations

12
Photoinduced intramolecular carbosulfonylation of alkynes: access to sulfone-containing dibenzazepines from sulfur dioxide DOI

Yanfang Yao,

Ziqing Yin,

Fu‐Sheng He

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(23), P. 2883 - 2886

Published: Jan. 1, 2021

A visible-light-driven three-component carbosulfonylation of terminal alkynes, DABCO (SO2)2 and aryldiazonium tetrafluoroborates is developed, leading to sulfone-containing dibenzazepines in moderate good yields under mild conditions.

Language: Английский

Citations

53
Metal-free C(sp2)-H perfluoroalkylsulfonylation and configuration inversion: Stereoselective synthesis of α-perfluoroalkylsulfonyl E-enaminones DOI
Qing Yu, Yunyun Liu, Jie‐Ping Wan

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(11), P. 3514 - 3517

Published: April 28, 2021

Language: Английский

Citations

48
Photoredox-catalyzed reaction of thianthrenium salts, sulfur dioxide and hydrazines DOI

Qiangwei Li,

Jiapian Huang, Zenghui Cao

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3781 - 3785

Published: Jan. 1, 2022

A photoredox-catalyzed reaction of thianthrenium salts, hydrazines and DABCO·(SO 2 ) is accomplished, providing diverse arenesulfonohydrazides in moderate to good yields under mild conditions.

Language: Английский

Citations

30
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