Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides DOI Creative Commons

Ciarán O’Shaughnessy,

Mukulesh Mondal,

Nessan J. Kerrigan

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 655 - 655

Published: Feb. 1, 2025

This review probes the recent developments in stereoselective reactions within area of sulfoxonium ylide chemistry since early 2000s. An abundance research has been applied to its emergence 1960s. There a continued effort then with work traditional areas, such as epoxidation, aziridination and cyclopropanation. Efforts have also novel olefination insertion reactions, develop methodologies using organocatalysis transition metal catalysis. The growing interrupted Johnson–Corey–Chaykovsky is described, whereby unexpected cyclopropanation epoxidation developed. In general, most observed mechanistic pathway ylides formal cycloaddition: (2 + 1) (e.g., epoxides, cyclopropanes, aziridines), (3 oxetanes, azetidines), (4 indanones, indolines). involves formation zwitterionic intermediate through nucleophilic addition carbanion an electrophilic site. intramolecular cyclization occurs, constructing cyclic product. Insertion X–H bonds X = S, N or P) are observed, protonation followed by X, form inserted

Language: Английский

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors DOI
Jiarong Shi, Lianggui Li, Yang Li

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(7), P. 3892 - 4044

Published: Feb. 18, 2021

Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In past 20 years, chemists witnessed a resurgence aryne chemistry, which is mainly attributed by extensive utilization Kobayashi's method, fluoride-induced removal TMS group with concomitant departure its ortho OTf on o-silylaryl triflates. Nowadays, triflates frequently employed precursors. This review provides an overview history methodological achievements, synthesis natural products, bioactive molecules, polycyclic aromatic hydrocarbons.

Language: Английский

Citations

298
Rh(III)-Catalyzed Cascade Reactions of Sulfoxonium Ylides with α-Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones DOI
Xi Chen, Muhua Wang, Xinying Zhang

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(8), P. 2541 - 2545

Published: April 8, 2019

An unprecedented cascade reaction of benzoyl sulfoxonium ylides with α-diazocarbonyl compounds leading to the formation highly functionalized naphthalenones containing a β-ketosulfoxonium ylide moiety is presented. Promisingly, naphthalenone derivative thus obtained was found be versatile intermediate toward diversely naphthalene derivatives including substituted 1-naphthol, 2-hydroxynaphthalen-1(2H)-one, naphthalen-1,2-dione, and 2-(methylsulfinyl)naphthalen-1-ol.

Language: Английский

Citations

133
RuII-Catalyzed/NH2-Assisted Selective Alkenyl C–H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines DOI
Pu Chen, Jiang Nan, Yan Hu

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(12), P. 4812 - 4815

Published: June 13, 2019

A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C–H activation as one-carbon coupling partners. Various 2-acylquinolines could be obtained good yields and excellent functional group tolerance. Moreover, potential synthetic application this methodology exemplified by several chemical transformations.

Language: Английский

Citations

105
Asymmetric transformations from sulfoxonium ylides DOI Creative Commons
Clarice A. D. Caiuby, Lucas G. Furniel, Antonio C. B. Burtoloso

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 13(5), P. 1192 - 1209

Published: Dec. 8, 2021

Sulfoxonium ylides are important surrogates for diazo compounds, and their use in industry as safer alternatives has been evaluated during recent years. Beyond the known classical transformations, these have also used a surprising plethora of novel intrinsic chemical reactions, especially Bench stability handling an advantage this class organosulfur molecules. Despite this, efficient asymmetric specifically catalytic enantioselective versions, only recently reported, there specific reasons this. This perspective article covers topic from first studies up to latest advances, giving personal perspectives showing main challenges area coming

Language: Английский

Citations

94
Iridium-catalyzed B–H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls DOI
Shang‐Shi Zhang, Hui Xie, Bing Shu

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(3), P. 423 - 426

Published: Dec. 4, 2019

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields most cases (51 examples; up 84%). This practical scalable reaction showed broad substrate scope, high functional-group compatibility could be applied late-stage modification structurally complex drug compounds. Further synthetic applications were also demonstrated.

Language: Английский

Citations

74
Synthesis of C6-Substituted Isoquinolino[1,2-b]quinazolines via Rh(III)-Catalyzed C–H Annulation with Sulfoxonium Ylides DOI
Jin Zhang, Xiaogang Wang, Di Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(5), P. 3192 - 3201

Published: Jan. 16, 2020

We report the synthesis of C6-substituted isoquinolino[1,2-b]quinazolinones via rhodium(III)-catalyzed C–H annulation with sulfoxonium ylides and evaluation cytotoxic activity scaffold. This activation approach enables most straightforward convergent isoquinolino[1,2-b]quinazolines reported to date. operationally simple method is compatible a wide variety ylide arene coupling partners, permitting access diverse isoquinolino[1,2-b]quinazolines. shows high atom economy, generating H2O dimethyl sulfoxide (DMSO) as by-products. scalable operates exquisite N-lactam cyclization selectivity, thus enabling expedient new heterocyclic analogues featuring promising properties.

Language: Английский

Citations

67
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides DOI Creative Commons
Patrícia B. Momo, Alexandria N. Leveille, Elliot H. E. Farrar

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(36), P. 15554 - 15559

Published: April 30, 2020

Abstract The first example of enantioselective S−H insertion reactions sulfoxonium ylides is reported. Under the influence thiourea catalysis, excellent levels enantiocontrol (up to 95 % ee ) and yields 97 %) are achieved for 31 examples in aryl thiols α‐carbonyl ylides.

Language: Английский

Citations

63
Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides DOI
Shuai Zhu, Kai Shi, Hao Zhu

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(4), P. 1504 - 1509

Published: Feb. 11, 2020

An unprecedented copper-catalyzed reaction of sulfoxonium ylides and anthranils is reported that enables an easy access to 2,3-diaroylquinolines through a [4+1+1] annulation. Copper-catalyzed homocoupling provided α,α,β-tricarbonyl ylides, which provides strategy extend the carbon chain C–C bond formation. The utility products as well mechanistic details process are presented.

Language: Английский

Citations

61
Ruthenium-Catalyzed Chemoselective N–H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides DOI
Xiaofeng Liu, Ying Shao, Jiangtao Sun

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(3), P. 1038 - 1043

Published: Jan. 21, 2021

A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, affording N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to achieve this unprecedented N–H rather than O–H insertion reaction is the use CpRu(PPh3)2Cl as catalyst sulfoxonium ylides alkylation reagents. Moreover, protocol also amenable 7-azaindoles by slightly varying conditions. Furthermore, sulfonium are suitable reagents, providing selectivity.

Language: Английский

Citations

49
Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones DOI
Shaoyong Chen, Yao‐Fu Zeng,

Wen‐Xuan Zou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4286 - 4291

Published: June 2, 2023

Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as active intermediate process 2,3,4,5-tetrasubstituted formation, while 2,3,5,6-tetrasubstituted generated direct [3 + 3] annulation under metal-free conditions. Further synthetic applications also demonstrated.

Language: Английский

Citations

22