Rh(III)-Catalyzed Cascade Reactions of Sulfoxonium Ylides with α-Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones

Organic Letters, Journal Year: 2019, Volume and Issue: 21(8), P. 2541 - 2545

Published: April 8, 2019

An unprecedented cascade reaction of benzoyl sulfoxonium ylides with α-diazocarbonyl compounds leading to the formation highly functionalized naphthalenones containing a β-ketosulfoxonium ylide moiety is presented. Promisingly, naphthalenone derivative thus obtained was found be versatile intermediate toward diversely naphthalene derivatives including substituted 1-naphthol, 2-hydroxynaphthalen-1(2H)-one, naphthalen-1,2-dione, and 2-(methylsulfinyl)naphthalen-1-ol.

Language: Английский

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Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Journal Year: 2018, Volume and Issue: 360(19), P. 3781 - 3787

Published: July 12, 2018

Abstract A highly chem‐ and regioselective synthesis of diversely substituted benzo[ a ]carbazoles indolo[2,1‐ ]‐isoquinolines through Rh(III)‐catalyzed cascade reactions 2‐arylindoles with sulfoxonium ylides is presented. To be specific, treatment 2‐arylindoles, 2‐arylindole‐3‐carbaldehydes, 2‐arylindole‐3‐carbonitriles or 2‐aryl‐3‐methylindoles under the catalysis Rh(III) led to selective formation 6‐aryl/alkyl ]carbazoles, 5‐acylbenzo[ 6‐amino‐5‐acylbenzo[ 12‐methylindolo[2,1‐ ]isoquinolines, respectively. Mechanistically, title compounds involves process including metalation inert C( sp 2 )−H bond, migratory insertion ylide into carbon‐metal bond via an in situ carbenoid formation, protodemetalation, condensation. our knowledge, this first example which β‐carbonyl were used as stable carbene precursors bifunctional C2 synthons afford ]isoquinolines. magnified image

Language: Английский

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Cp*M-Catalyzed Direct Annulation with Terminal Alkynes and Their Surrogates for the Construction of Multi-Ring Systems

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(17), P. 9747 - 9757

Published: Aug. 3, 2020

Transition-metal-catalyzed C–H activation followed by oxidative cyclization with unsaturated coupling partners has been a valuable synthetic tool for the multiring molecular scaffolds. This Perspective introduces recent progress on Cp*M-catalyzed (M = Co, Rh, and Ir) direct annulation of functionalized arenes terminal alkynes their equivalents through bond cleavage. The highlighted examples are categorized according to 10 different types reagents used in transformations. representative conditions, selected reaction scope, key mechanistic aspects briefly summarized.

Language: Английский

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Sulfoxonium ylides: simple compounds with chameleonic reactivity

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

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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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Recent Applications of α-Carbonyl Sulfoxonium Ylides in Rhodium- and Iridium-Catalyzed C–H Functionalizations

Synlett, Journal Year: 2018, Volume and Issue: 30(01), P. 21 - 29

Published: Sept. 5, 2018

Sulfoxonium ylides are a special type of sulfur that serve as new C1 or C2 synthons recently developed for use in C–H functionalization to access acylmethylated cyclized compounds through the formation metal carbene species. Many excellent works have reported syntheses various useful skeletons from these versatile synthons. These developments not previously been completely investigated reviewed. In this review, we summarize recent advances α-carbonyl sulfoxonium functionalizations, including ortho-C–H acylmethylation reactions and activation/cyclization reactions. Table Contents 1 Introduction 2 Ortho-C–H Acylmethylation Reactions 3 Activation/Cyclization 3.1 Anilines Enamines 3.2 Azobenzenes 3.3 N-Methoxybenzamide 3.4 Imines 3.5 N-Azoloimines 3.6 Benzoylacetonitriles 3.7 Benzoyl Ylides 4 Conclusion

Language: Английский

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Synthesis of indoles and quinazolines via additive-controlled selective C–H activation/annulation of N-arylamidines and sulfoxonium ylides

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(28), P. 4039 - 4042

Published: Jan. 1, 2019

Selective synthesis of indoles and quinazolines was achieved through a precise control C–H activation/annulation by changing additives.

Language: Английский

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Cp*Co(III)-Catalyzed C–H Acylmethylation of Arenes by Employing Sulfoxonium Ylides as Carbene Precursors

Organic Letters, Journal Year: 2018, Volume and Issue: 20(18), P. 5981 - 5984

Published: Sept. 12, 2018

A Cp*Co(III)-catalyzed C-H bond functionalization of a range arenes by employing sulfoxonium ylides as carbene precursors instead diazo compounds and other has been established. This reaction is highly efficient without any additive, possesses high step atom economies, tolerates functional groups.

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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Ruthenium(ii)-catalyzed selective C–H bond activation of imidamides and coupling with sulfoxonium ylides: an efficient approach for the synthesis of highly functional 3-ketoindoles

Organic Chemistry Frontiers, Journal Year: 2019, Volume and Issue: 6(8), P. 1183 - 1188

Published: Jan. 1, 2019

Ruthenium-catalyzed selective C–H bond activation of imidamides and annulation sulfoxonium ylides were achieved, which afforded a series 3-ketoindole derivatives in good yields, with functional group compatibility.

Language: Английский

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