Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I(III)/S(VI) Ylides DOI
Shang‐Shi Zhang,

Jiaohang Wei,

Qiong Hu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation I(III)/S(VI) with 1,3-dicarbonyls. By slight modification reaction conditions, controllable alkylation-hydroxylation and dialkylation were achieved. This strategy affords a diverse array α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement sulfoxonium highlight divergent reactivity ylides.

Язык: Английский

HFIP in Organic Synthesis DOI
Hashim F. Motiwala,

Ahlam M. Armaly,

Jackson G. Cacioppo

и другие.

Chemical Reviews, Год журнала: 2022, Номер 122(15), С. 12544 - 12747

Опубликована: Июль 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Язык: Английский

Процитировано

325

Sulfoxonium ylides: simple compounds with chameleonic reactivity DOI
Giorgiana Denisa Bisag, Silvia Ruggieri, Mariafrancesca Fochi

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(43), С. 8793 - 8809

Опубликована: Янв. 1, 2020

Sulfur ylides first disclosed in 1930 started to gain more attention the 1960s, thanks mainly studies by Corey and Chaykovsky on their use for preparation of strained rings. More recently, chemistry these compounds has experienced important growth, part due similarity reactivities with diazo compounds. This short review provides an overview great assortment reactions sulfoxonium ylides, outlining a comparison between congeners: sulfonium Insertion reactions, cyclisation ring-opening are highlighted, giving particular catalytic asymmetric methodologies.

Язык: Английский

Процитировано

117

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

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)–H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones DOI
Bingnan Du, Yuxin Ouyang,

Qishu Chen

и другие.

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(37), С. 14962 - 14968

Опубликована: Сен. 8, 2021

A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C–H bond amidation of unactivated alkenes. Due the preference for five-membered nickelacycle formation, chain-walking isomerization initiated by NiH insertion an alkene can be terminated at γ-methylene site from moiety. By employing 2,9-dibutyl-1,10-phenanthroline (L4) as ligand and dioxazolones reagent, occurs γ-C(sp3)–H bonds afford amide products in up 90% yield (>40 examples) with remarkable regioselectivity (up 24:1 rr).

Язык: Английский

Процитировано

79

Transition metal-catalyzed C–H functionalizations of indoles DOI
Pravin Kumar, Prajyot Jayadev Nagtilak, Manmohan Kapur

и другие.

New Journal of Chemistry, Год журнала: 2021, Номер 45(31), С. 13692 - 13746

Опубликована: Янв. 1, 2021

This review summarises a wide range of transformations on the indole skeleton, including arylation, alkenylation, alkynylation, acylation, nitration, borylation, and amidation, using transition-metal catalyzed C–H functionalization as key step.

Язык: Английский

Процитировано

73

Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions DOI
Anil Kumar, Mahadev Sharanappa Sherikar, Vinayak Hanchate

и другие.

Tetrahedron, Год журнала: 2021, Номер 101, С. 132478 - 132478

Опубликована: Окт. 8, 2021

Язык: Английский

Процитировано

71

Co(III), Rh(III) & Ir(III)‐Catalyzed Direct C−H Alkylation/Alkenylation/Arylation with Carbene Precursors DOI
Saiprasad Nunewar, Sanjeev Kumar,

Srilakshmi Talakola

и другие.

Chemistry - An Asian Journal, Год журнала: 2021, Номер 16(5), С. 443 - 459

Опубликована: Янв. 15, 2021

Metal carbenes play a pivotal role in transition-metal-catalyzed synthetic transfer reactions. The metal carbene is generated either from diazo compound through facile extrusion of N2 with catalyst or situ other sources like triazoles, pyriodotriazoles, sulfoxonium ylides and iodonium-ylide. On the hand, Co(III), Rh(III) & Ir(III)-catalyzed C-H functionalizations have been well established as key step to enable construction various transformations. Interestingly, recent years, merging these two concepts activation migratory insertion gained much attention, particular group 9 metal-catalyzed arene precursors via insertion. In this review, we summarize advances direct alkylation/alkenylation/arylation also discuss intermediates within catalytic cycles.

Язык: Английский

Процитировано

66

Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides DOI

Pratiksha Bhorali,

Sabera Sultana, Sanjib Gogoi

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(4)

Опубликована: Март 23, 2022

Abstract In recent years, the transition‐metal‐catalyzed functionalization reactions of sulfoxonium ylides have been explored extensively because their usefulness as carbene‐transfer agents, since they can produce metal carbenes through catalysis. Moreover, are safer and advantages simple handling good stability over other counterparts like diazo‐compounds. This review article attempts to highlight advances in metal‐catalyzed C−H ylides.

Язык: Английский

Процитировано

41

Recent Advances in Metal‐catalyzed Alkylation, Alkenylation and Alkynylation of Indole/indoline Benzenoid Nucleus DOI
Sourav Pradhan,

Pinaki Bhusan De,

Tariq A. Shah

и другие.

Chemistry - An Asian Journal, Год журнала: 2020, Номер 15(24), С. 4184 - 4198

Опубликована: Ноя. 9, 2020

Selective editing of the benzenoid C-H bonds (C4-C7) in indoles/indolines has received great interest because functionalized are featured many marketed drugs and natural products. Transition-metal-catalyzed directed functionalization thus been developed to manipulate core through C-C C-heteroatom bond formation. This review covers recent advances selective forming reactions, alkylation, alkenylation alkynylation, over ring using metal catalysis.

Язык: Английский

Процитировано

56

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

и другие.

Organic Letters, Год журнала: 2021, Номер 23(3), С. 1038 - 1043

Опубликована: Янв. 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.

Язык: Английский

Процитировано

50