Rhodium(III)-Catalyzed Chemo-divergent Couplings of Sulfoxonium Ylides with Oxa/azabicyclic Olefins DOI
Peiyuan Wang, Youwei Xu, Jiaqiong Sun

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(20), P. 8459 - 8463

Published: Oct. 7, 2019

Rh(III)-catalyzed C–H functionalization of sulfoxonium ylides has been realized in chemo-divergent couplings with oxa/azabicyclic olefins. Divergent [4 + 2] annulation and alkylation have attained under controlled condition. In the system, ylide functions as a traceless oxidizing directing group. contrast, introduction PivOH shunted selectivity to ring-retentive alkylation.

Language: Английский

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

70
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

40
Ruthenium (II)‐Catalyzed Oxidant‐Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines DOI

Xinxia Shi,

Rongchao Wang,

Xiaofei Zeng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2018, Volume and Issue: 360(21), P. 4049 - 4053

Published: Aug. 20, 2018

Abstract A ruthenium‐catalyzed direct mono‐C−H functionalization/annulation cascade reaction of benzimidates and sulfoxonium ylides has been developed. The proceeds smoothly with a broad range substrates, giving access to variety isoquinoline derivatives in moderate good yields using an organic acid additive under oxidant free conditions. magnified image

Language: Английский

Citations

77
Ruthenium(IV) Intermediates in C−H Activation/Annulation by Weak O‐Coordination DOI
Yu‐Feng Liang, Long Yang, Torben Rogge

et al.

Chemistry - A European Journal, Journal Year: 2018, Volume and Issue: 24(62), P. 16548 - 16552

Published: Sept. 25, 2018

Abstract Ruthenium(IV) complexes were identified as key intermediates of C−H/O−H activations by weak O ‐coordination. Thus, the annulations sulfoxonium ylides benzoic acids provided expedient access to diversely‐decorated isocoumarins with ample scope. Detailed experimental and computational studies strong support for a facile BIES‐C−H activation, along cyclometalated ruthenium(IV) within versatile ruthenium(II/IV) catalysis regime (BIES=base‐assisted internal electrophilic substitution).

Language: Английский

Citations

77
Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones DOI
Chunsheng Li, Meng Li,

Wentao Zhong

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(4), P. 872 - 875

Published: Feb. 6, 2019

The first examples of palladium-catalyzed allylic C–H oxidative allylation sulfoxonium ylides to afford the corresponding conjugated dienones with moderate good yields have been established. features this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.

Language: Английский

Citations

73
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

73
Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls DOI Creative Commons

Daniel Clare,

Benjamin C. Dobson,

Phillip A. Inglesby

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(45), P. 16198 - 16202

Published: Sept. 11, 2019

The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help a directing group has remained so far neglected area, despite advantageous safety profile ylides. Described herein are cyclizations onto benzenes, benzofurans N-p-toluenesulfonyl indoles in presence base HFIP, whereas pyrroles N-methyl undergo cyclization an iridium catalyst. Significantly, these two sets conditions chemospecific for each groups substrates.

Language: Английский

Citations

68
Iridium(III)-Catalyzed Tandem Annulation Synthesis of Pyrazolo[1,2-α]cinnolines from Pyrazolones and Sulfoxonium Ylides DOI

Chen‐Fei Liu,

Man Liu, Lin Dong

et al.

The Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 84(1), P. 409 - 416

Published: Dec. 6, 2018

A highly efficient iridium-catalyzed cascade annulation of pyrazolones and sulfoxonium ylides to access various pyrazolo[1,2-α]cinnoline derivatives has been achieved. This novel approach expanded the application scope coupling partners ylides. The control experiments were performed give insight into mechanism this reaction.

Language: Английский

Citations

62
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

60
Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C–H Activation/Cyclopropanation Cascade DOI
Jiang Lou, Quannan Wang, Yong‐Gui Zhou

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(22), P. 9217 - 9222

Published: Nov. 5, 2019

Rhodium(III)-catalyzed annulative coupling of sulfoxonium ylides with allenoates was achieved, forming highly functionalized cyclopropanes a quaternary carbon center by means the ylide functionality as traceless bifunctional directing group and C4 synthon via an arene C–H activation cyclopropanation cascade. The protocol features simultaneous formation three new C–C bonds in one pot excellent diastereoselectivity. resultant products could be further transformed to diverse synthetically useful compounds.

Language: Английский

Citations

59