Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N–S Bond Activation of Sulfonamides DOI
Jing-Song Zhen, Xian Du, Xiaohong Xu

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(3), P. 1986 - 1991

Published: Jan. 21, 2022

A visible-light-mediated late-stage arylation of N–S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent bond arylation, demonstrating the advantages sulfonylation reagents. Additionally, mechanism research revealed that probably both EDA chemistry photoredox catalysis were responsible for formation sulfones. This methodology characterized broad substrate scope simple reaction conditions also high atom economy, since aldehyde synthesis recovered after workup reactions.

Language: Английский

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency DOI
Guglielmo Coppola, Serena Pillitteri, Erik V. Van der Eycken

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(6), P. 2313 - 2382

Published: Jan. 1, 2022

Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.

Language: Английский

Citations

161
A practical FeCl3/HCl photocatalyst for versatile aliphatic C–H functionalization DOI Creative Commons

Zhen-Yao Dai,

Shuo‐Qing Zhang, Xin Hong

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(5), P. 1211 - 1222

Published: April 20, 2022

Language: Английский

Citations

86
A reagent to access methyl sulfones DOI Creative Commons

Yaroslav Poplavskyi,

Vasyl Ripenko,

Sergei Bova

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 29, 2025

A chemical reagent to access methyl sulfones has been developed. Its reaction with various bis-nucleophiles leads the rapid formation of previously unknown heteroaromatic sulfones. Analogous strategy can also be used construct alkyl-, CHF2-, CF3- and even bicyclo[1.1.1]pentane-containing derivatives. These compounds have demonstrated a high potential for use in medicinal chemistry coordination chemistry. Methyl sulfone is standard polar substituent found different agro chemicals or drugs but due lack convenient efficient approaches them, are less investigated. Here authors report

Language: Английский

Citations

2
Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones DOI
Shuai Liang,

Kamil Hofman,

Marius Friedrich

et al.

ChemSusChem, Journal Year: 2021, Volume and Issue: 14(22), P. 4878 - 4902

Published: Sept. 3, 2021

Sulfones play a pivotal role in modern organic chemistry. They are highly versatile building blocks and find various applications as drugs, agrochemicals, or functional materials. Therefore, sustainable access to this class of molecules is great interest. Herein, the goal was provide summary on recent developments field sulfone synthesis. Advances existing limitations traditional approaches towards sulfones were reviewed selected examples. Furthermore, novel emerging technologies for more synthesis future directions discussed.

Language: Английский

Citations

91
Thianthrenium-enabled sulfonylation via electron donor-acceptor complex photoactivation DOI Creative Commons
Albert Granados, María Jesús Cabrera‐Afonso, Marcos Escolano

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(4), P. 898 - 907

Published: April 1, 2022

Sulfone-containing compounds are prevalent building blocks in pharmaceutical agents and other biomolecules, they serve as key intermediates the synthesis of complex scaffolds. During past decade, several methods have been developed to access sulfones. These strategies, however, require use strong reaction conditions, limiting their substrate scope. Recently, visible-light-mediated transformations emerged novel platforms unprecedented structural motifs. This report demonstrates thianthrenium-enabled sulfonylation via intra-complex charge transfer generate transient aryl- persistent sulfonyl radicals that undergo selective coupling alkyl- (hetero)aryl sulfones under ambient conditions. strategy allows retention halide handles, presenting a complementary approach transition metal-mediated photoredox couplings. Furthermore, this high functional group tolerance is amenable late-stage functionalization biomolecules. Mechanistic investigations support intermediacy electron donor-acceptor (EDA) complexes.

Language: Английский

Citations

67
Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts DOI
Fu‐Sheng He,

Ping Bao,

Zhimei Tang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(15), P. 2955 - 2960

Published: April 13, 2022

A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials functional group compatibility, enabling the introduction various functionalized sulfonyl groups into ketones. Furthermore, as one important industrial raw materials, methanol can be employed methyl source prepare α-methylsulfonated ketones through a intermediate for first time.

Language: Английский

Citations

63
Ligand-Enabled Gold-Catalyzed C(sp2)–S Cross-Coupling Reactions DOI
Akash G. Tathe, Nitin T. Patil

Organic Letters, Journal Year: 2022, Volume and Issue: 24(24), P. 4459 - 4463

Published: June 13, 2022

Herein we report C(sp2)-S cross-coupling reactions of aryl iodides and arylsulfonyl hydrazides under ligand-enabled, Au(I)/Au(III) redox catalysis. This strategy operates mild reaction conditions, requires no prefunctionalized coupling partner, works across several iodides. The utility this protocol is highlighted through the synthesis various medicinally relevant biaryl sulfones. mechanism supported with control experiments, mass spectrometry, NMR studies.

Language: Английский

Citations

43
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

25
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

23
Synthesis of Vinyl and 1,3‐Dienyl Sulfones Enabled by Photochemical Excitation of Halogen‐Bonding Complexes DOI Creative Commons
Helena F. Piedra, Carlos Valdés, Manuel Plaza

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1422 - 1429

Published: Feb. 1, 2024

Abstract The photochemical catalyst‐free radical‐based synthesis of vinyl and 1,3‐dienyl sulfones is disclosed. Mechanistic investigations support that the transformations rely on a visible‐light‐promoted activation halogen‐bonding complex, which formed between an alkenyl (or 1,3‐dienyl) bromide sodium sulfinate salt. reactions exhibit wide functional group tolerance (compatible with heteroatoms, electron‐withdrawing electron‐donating groups), finding application in structural modification biologically relevant molecules. Eventually, continuous flow protocol was developed to upscale these transformations.

Language: Английский

Citations

9