Ru^II-Catalyzed/NH₂-Assisted Selective Alkenyl C–H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines

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

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Transition Metal–Catalyzed Allylic C(sp³)–H Functionalization via η³‐Allylmetal Intermediate

Chinese Journal of Chemistry, Journal Year: 2019, Volume and Issue: 37(7), P. 720 - 743

Published: May 15, 2019

As an efficient and facile access to linear or branched allylic compounds, transition metal-catalyzed C(sp3)–H functionalization reaction via η3-allylmetal intermediates has gained increasing interest in recent years. Pd, Rh, Ru, Ir, Fe Co-catalyzed systems have all been successfully achieved, affording various compounds bearing a diverse set of functionalities. Herein, we provide comprehensive review this burgeoning field according different metal catalysts.

Language: Английский

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Rhodium-Catalyzed Reaction of Sulfoxonium Ylides and Anthranils toward Indoloindolones via a (4 + 1) Annulation

Organic Letters, Journal Year: 2019, Volume and Issue: 21(17), P. 6653 - 6657

Published: Aug. 19, 2019

A rhodium-catalyzed annulation between aroyl sulfoxonium ylides and anthranils has been developed to synthesize 10H-indolo[1,2-a]indol-10-one derivatives. This reaction started with an unpredented (4 + 1) toward N-(2-formylphenyl) indolones, proceeding the sequential ortho-amination of C–H bond in by insertion N–H carbene. Finally, Aldol condensation constructed second indole ring. procedure features formation two C–N bonds one C═C pot.

Language: Английский

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

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

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Iridium-catalyzed B–H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls

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

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Catalytic allylic functionalization via π-allyl palladium chemistry

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(38), P. 8647 - 8672

Published: Jan. 1, 2019

This review highlights the developments in palladium-catalyzed allylic C-H functionalization from early 2014 to present date. π-Allylpalladium chemistry emphasizes research originating less appealing stoichiometric Pd(ii) based activation day green, step- and atom-economical sustainable strategy, wherein hydrogen atom becomes "leaving group". constitutes a direct method, which is essentially catalytic presence of terminal oxidant regenerate Pd(ii)-species Pd(0). The availability chiral ligands, under oxidative conditions, has paved way realize asymmetric Tsuji-Trost alkylations.

Language: Английский

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Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

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

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Synthesis of C6-Substituted Isoquinolino[1,2-b]quinazolines via Rh(III)-Catalyzed C–H Annulation with Sulfoxonium Ylides

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

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Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides

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

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Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C–H Activation/Cyclopropanation Cascade

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

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