Bis(1,1‐dimethylethyl)[2′,4′,6′‐tris‐(1‐methylethyl)[1,1′‐biphenyl]‐2‐yl]‐phosphine and Dicyclohexyl[2′,4′,6′‐tris(1‐methylethyl)[1,1′‐biphenyl]‐2‐yl]phosphine DOI
E. Herrero-Gómez, Antonio M. Echavarren, Ekaterina V. Vinogradova

и другие.

Encyclopedia of Reagents for Organic Synthesis, Год журнала: 2021, Номер unknown, С. 1 - 17

Опубликована: Апрель 30, 2021

XPhos [564483-18-7] C33H49P (MW 476.72) InChI = 1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3 InChIKey UGOMMVLRQDMAQQ-UHFFFAOYSA-N (bulky, electron-rich monophosphine used as ligand in transition-metal-catalyzed reactions, especially the context of Pd chemistry) Alternative Names: 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl, XPhos. Physical Data: mp 187–190 °C. Solubility: soluble most organic solvents. Form Supplied in: white solid; widely available. t-BuXPhos [564483-19-8] C29H45P 424.65) 1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3 SACNIGZYDTUHKB-UHFFFAOYSA-N Pd-catalyzed reactions) 2-di-t-butylphosphino-2′,4′,6′-triisopropyl t-BuXPhos, di-t-BuXPhos. 148–151 Handling, Storage, and Precautions: oxidation these related phosphines has been examined.1 The presence three isopropyl groups on 2′, 4′, 6′ positions nonphosphine-containing ring reduces their reactivity toward atmospheric oxygen to less than 3% at room temperature toluene solution after 65 h. Under an atmosphere O2 100 °C for h only 28% 13% phosphine oxide are formed from tert-BuXPhos, respectively. Preparative Method: can be prepared by reaction 2-bromochlorobenzene with Grignard reagent 1-bromo-2,4,6-triisopropylbenzene THF, followed addition catalytic CuCl ClPCy2. A similar procedure using CIPtBu2 was applied synthesis t-BuXPhos.2

Язык: Английский

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

и другие.

Chemical Science, Год журнала: 2021, Номер 13(5), С. 1192 - 1209

Опубликована: Дек. 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

Язык: Английский

Процитировано

95
Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins DOI
Chuanliu Yin, Lianghao Li, Chuanming Yu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(5), С. 1112 - 1116

Опубликована: Янв. 1, 2022

The direct synthesis of isocoumarin skeletons has been realized through the Rh( iii )-catalyzed [3 + 3] annulation sulfoxonium ylides and iodonium under mild conditions.

Язык: Английский

Процитировано

33
Synthesis of α-Carbonyl-α′-amide Sulfoxonium Ylides from Isocyanates with Complete Atom Economy DOI

Ajay Kant Gola,

Ajay Sharma, Satyendra Kumar Pandey

и другие.

Organic Letters, Год журнала: 2023, Номер 25(7), С. 1214 - 1217

Опубликована: Фев. 9, 2023

An efficient catalyst- and additive-free facile synthesis of α-carbonyl-α′-amide sulfoxonium ylides from isocyanates β-ketosulfoxonium with complete atom economy has been described. The adorned various functional groups were well-tolerated afforded moderate to high yields the ylide derivatives. Finally, using large-scale reactions converting synthesized into other valuable compounds, we demonstrated practicality this synthetic method.

Язык: Английский

Процитировано

18
A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides DOI

Wen‐Xuan Zou,

Qiong Hu,

Dan‐Ting Shen

и другие.

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5811 - 5816

Опубликована: Июнь 28, 2024

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.

Язык: Английский

Процитировано

7
Photochemical Reactions of Sulfur Ylides DOI
Radell Echemendía,

Kauê C. Capellaro,

Antonio C. B. Burtoloso

и другие.

Current Organic Chemistry, Год журнала: 2024, Номер 28(13), С. 978 - 990

Опубликована: Май 6, 2024

Abstract: Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical have become indispensable tools accessing molecular structures, such as pharmaceuticals natural products. The ability of sulfur ylides participate in these diverse processes has made them the synthetic chemist's toolbox. use transformations garnered significant attention chemistry community, they serve powerful intermediates several transformations. This review article presents a comprehensive overview mediated by ylides. Herein, we describe key aspects reactivity presence light. compounds can be classified into three categories: energy acceptors, electron donors, trapping reagents.

Язык: Английский

Процитировано

4
Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water DOI
Behzad Zeynizadeh,

Farkhondeh Mohammad Aminzadeh,

Hossein Mousavi

и другие.

Research on Chemical Intermediates, Год журнала: 2021, Номер 47(8), С. 3289 - 3312

Опубликована: Май 3, 2021

Язык: Английский

Процитировано

25
Perhaloacylation of α-Carbonyl Sulfoxonium Ylides DOI
Varun Anand, Namrata Rastogi

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 2, 2025

A mild and efficient protocol for the perhaloacylation of α-carbonyl sulfoxonium ylides has been developed. The commercially available perfluoro- perchloroacid anhydrides were used as acylating agents in catalyst- additive-free reactions to access α-carbonyl-α'-perhaloacyl high yields. reaction offers a simple method prepare valuable polyfluorinated organosulfur molecules.

Язык: Английский

Процитировано

0
Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides DOI Creative Commons

Ciarán O’Shaughnessy,

Mukulesh Mondal,

Nessan J. Kerrigan

и другие.

Molecules, Год журнала: 2025, Номер 30(3), С. 655 - 655

Опубликована: Фев. 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

Язык: Английский

Процитировано

0
Catalyst‐Free Direct Hydrocarbonation of Terminal Alkynes Toward E‐Alkene Substituted Stabilized Sulfoxonium Ylides DOI Creative Commons

Haiting Wu,

Yougen Xu,

Lin An

и другие.

Advanced Science, Год журнала: 2025, Номер unknown

Опубликована: Апрель 2, 2025

Amide and alkene moieties are frequently found in natural products privileged structures pharmaceuticals agrochemicals. Moreover, vinyl sulfoxonium ylide can be converted into a broad range of high-value compounds, thus they have been widely employed organic synthesis. However, the synthesis alkene-substituted amide-sulfoxonium ylides via intermolecular hydrocarbonation alkynes remains underexplored. This study describes development high-throughput approach to provide diverse functionalized E-alkene substituted (hetero)amide-sulfoxonium ylides. The reaction occurs under mild metal-free conditions, employing as highly effective nucleophiles, which participate Michael addition reactions with various alkynes, such esters, thioesters, ketones, amides, sulfones. low-cost, operationally simple has substrate scope, high functional group compatibility, excellent regio- stereoselectivity, making it suitable for transformation structurally complex molecules. Furthermore, obtained stabilized directly useful valuable 1,5-dicarbonyl thiabenzene 1-oxide compounds.

Язык: Английский

Процитировано

0
Photocatalytic Approach Toward the Synthesis of Amides via S–C Cleavage: A Mild Approach DOI
Shikha Pandey, Sandeep Kumar, Vishal Singh

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

A metal-free photocatalytic methodology for the synthesis of amides has been developed using eosin Y as a photocatalyst under ambient conditions. This approach provides sustainable and efficient alternative amide formation by eliminating need metal catalysts, operates efficiently at room temperature. The use promotes high selectivity reactivity, providing green cost-effective pathway amides.

Язык: Английский

Процитировано

0