Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(14), P. 8701 - 8780

Published: June 25, 2019

Organosulfur compounds have long played a vital role in organic chemistry and the development of novel chemical structures architectures. Prominent among these organosulfur are those involving sulfur(IV) center, which been subject countless investigations over more than hundred years. In addition to list textbook sulfur-based reactions, there has sustained interest organosulfur(IV) recent Of particular within is ease with synthetic chemist can effect wide range transformations through either bond formation or cleavage at sulfur. This review aims cover developments past decade molecules provide insight into both reactions critically rely on this versatile element diverse scaffolds that thereby be synthesized.

Language: Английский

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Rhodium(iii)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C–H activation

Organic Chemistry Frontiers, Journal Year: 2017, Volume and Issue: 5(6), P. 998 - 1002

Published: Dec. 22, 2017

Sulfoxonium ylides acts as a bifunctional C₂-synthon in Rh(iii)-catalyzed redox-neutral annulative coupling with arenes for the synthesis of N-heterocycles and carbocycles.

Language: Английский

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Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C–H Bonds toward Fused Heteroarenes

Organic Letters, Journal Year: 2018, Volume and Issue: 20(5), P. 1396 - 1399

Published: Feb. 22, 2018

A rhodium-catalyzed annulation between ethyl benzimidates and α- aroyl sulfur ylides was developed, affording a series of pyrano[4,3,2-ij]isoquinoline derivatives in moderate to good yields with functional group compatibility. The procedure featured dual ortho-C–H functionalization cyclization one pot. optoelectronic properties those fused heteroarenes were tested by UV/vis fluorescence spectrometers.

Language: Английский

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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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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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Synthesis of (2H)-Indazoles through Rh(III)-Catalyzed Annulation Reaction of Azobenzenes with Sulfoxonium Ylides

The Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 83(7), P. 4070 - 4077

Published: March 16, 2018

The rhodium(III)-catalyzed C–H functionalization followed by intramolecular annulation reactions between azobenzenes and sulfoxonium ylides is described. This protocol leads to the efficient formation of 3-acyl (2H)-indazoles with a range substrate scope. A high level chemoselectivity functional group tolerance this transformation were also observed.

Language: Английский

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