Condition-Dependent Selective Synthesis of Indolo[1,2-c]quinazolines and Indolo[3,2-c]quinolines from 2-(1H-Indol-2-yl)anilines and Sulfoxonium Ylides DOI
Guang Chen,

Xinyuan Cai,

Xinying Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 9815 - 9828

Published: July 15, 2022

In this paper, a selective synthesis of indolo[1,2-c]quinazolines and indolo[3,2-c]quinolines through the cascade reactions 2-(1H-indol-2-yl)anilines with sulfoxonium ylides is presented. The formation products involves generation carbene species from ylide its N–H bond insertion reaction 2-(1H-indol-2-yl)aniline followed by deoxygenative imine formation, intramolecular N– or C– nucleophilic addition aromatization. This switchable was condition-dependent. presence K2CO3 in CH3CN, mainly furnished indolo[1,2-c]quinazolines. HOAc dioxane, it selectively afforded indolo[3,2-c]quinolines. addition, direct C–H/N–H functionalization obtained provides convenient access to polycyclic heteroaromatic compounds. These novel protocols have advantages such as readily accessible substrates, easily tunable selectivity, good compatibility diverse functional groups, use air cost-free sustainable oxidant.

Language: Английский

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

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(43), P. 8793 - 8809

Published: Jan. 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.

Language: Английский

Citations

117
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

96
Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions DOI
Anil Kumar, Mahadev Sharanappa Sherikar, Vinayak Hanchate

et al.

Tetrahedron, Journal Year: 2021, Volume and Issue: 101, P. 132478 - 132478

Published: Oct. 8, 2021

Language: Английский

Citations

71
Ruthenium(ii)-catalyzed synthesis of CF3-isoquinolinones via C–H activation/annulation of benzoic acids and CF3-imidoyl sulfoxonium ylides DOI

Si Wen,

Yu‐Qing Zhang,

Qingyu Tian

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(16), P. 4388 - 4393

Published: Jan. 1, 2022

The synthesis of 3-trifluoromethylisoquinolinones by a ruthenium( ii )-catalyzed C–H activation/annulation reaction benzoic acids and CF 3 -imidoyl sulfoxonium ylides has been achieved.

Language: Английский

Citations

43
Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides DOI

Pratiksha Bhorali,

Sabera Sultana, Sanjib Gogoi

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(4)

Published: March 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.

Language: Английский

Citations

41
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

64
Thioether-Directed C4-Selective C–H Acylmethylation of Indoles Using α-Carbonyl Sulfoxonium Ylides DOI

Chandrababu Naidu Kona,

Yuji Nishii, Masahiro Miura

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(12), P. 4806 - 4811

Published: June 1, 2020

Site-selective direct functionalization of an indole benzenoid core has been a great challenge due to its inherently poor reactivity. We herein demonstrate iridium-catalyzed C4-selective acylmethylation indoles using α-carbonyl sulfoxonium ylides as carbene precursors. This method exhibits high efficiency and broad functional group compatibility. The directing was easily removed or converted other functionalities after the catalysis. potential synthetic utility coupling products highlighted by constructing medium-sized polycyclic indoles.

Language: Английский

Citations

59
Rhodium(III)‐Catalyzed Asymmetric [4+1] and [5+1] Annulation of Arenes and 1,3‐Enynes: A Distinct Mechanism of Allyl Formation and Allyl Functionalization DOI
Jiaqiong Sun, Weiliang Yuan, Rong Tian

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(50), P. 22706 - 22713

Published: Sept. 4, 2020

Abstract We report chiral Rh III cyclopentadienyl‐catalyzed enantioselective synthesis of lactams and isochromenes through oxidative [4+1] [5+1] annulation, respectively, between arenes 1,3‐enynes. The reaction proceeds a C−H activation, alkenyl‐to‐allyl rearrangement, nucleophilic cyclization cascade. mechanisms the annulations were elucidated by combination experimental computational methods. DFT studies indicated that, following activation alkyne insertion, alkenyl intermediate undergoes δ ‐hydrogen elimination allylic via six‐membered ring transition state to produce enallene hydride intermediate. Subsequent insertion allyl rearrangement affords several rhodium(III) intermediates, rare η 4 ene‐allyl species with π‐agostic interaction SN 2 ′‐type external attack nitrogen nucleophile, instead C−N reductive elimination, as stereodetermining step.

Language: Английский

Citations

51
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

50
Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins DOI
Chuanliu Yin, Lianghao Li, Chuanming Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(5), P. 1112 - 1116

Published: Jan. 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.

Language: Английский

Citations

34