A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

Chemical Society Reviews, Год журнала: 2018, Номер 47(17), С. 6603 - 6743

Опубликована: Янв. 1, 2018

The present review is devoted to summarizing the recent advances (2015-2017) in field of metal-catalysed group-directed C-H functionalisation. In order clearly showcase molecular diversity that can now be accessed by means directed functionalisation, whole organized following directing groups installed on a substrate. Its aim comprehensive reference work, where specific group easily found, together with transformations which have been carried out it. Hence, primary format this schemes accompanied concise explanatory text, are ordered sections according their chemical structure. feature typical substrates used, products obtained as well required reaction conditions. Importantly, each example commented respect most important positive features and drawbacks, aspects such selectivity, substrate scope, conditions, removal, greenness. targeted readership both experts functionalisation chemistry (to provide overview progress made last years) and, even more so, all organic chemists who want introduce way thinking for design straightforward, efficient step-economic synthetic routes towards molecules interest them. Accordingly, should particular also scientists from industrial R&D sector. overall goal promote application reactions outside research dedicated method development establishing it valuable archetype contemporary R&D, comparable role cross-coupling play date.

Язык: Английский

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

Chemical Reviews, Год журнала: 2019, Номер 119(14), С. 8701 - 8780

Опубликована: Июнь 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.

Язык: Английский

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HFIP in Organic Synthesis

Chemical Reviews, Год журнала: 2022, Номер 122(15), С. 12544 - 12747

Опубликована: Июль 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Язык: Английский

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Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C–H Acylmethylation of Arenes

Organic Letters, Год журнала: 2017, Номер 19(19), С. 5256 - 5259

Опубликована: Сен. 13, 2017

Sulfoxonium ylides act as an efficient carbene precursor in rhodium(III)-catalyzed C-H acylmethlyation of a variety arenes assisted by different chelating groups, and both aryl- alkyl-substituted β-carbonyl sulfoxonium are applicable. The system proceeded under redox-neutral conditions with broad scope, high efficiency, functional group tolerance.

Язык: Английский

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Rhodium(iii)-catalyzed chemodivergent annulations between N-methoxybenzamides and sulfoxonium ylides via C–H activation

Chemical Communications, Год журнала: 2018, Номер 54(6), С. 670 - 673

Опубликована: Янв. 1, 2018

Rhodium-catalyzed and acid-controlled chemodivergent annulations between N-methoxybenzamides sulfoxonium ylides have been realized.

Язык: Английский

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

Organic Chemistry Frontiers, Год журнала: 2017, Номер 5(6), С. 998 - 1002

Опубликована: Дек. 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.

Язык: Английский

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

Organic Letters, Год журнала: 2018, Номер 20(5), С. 1396 - 1399

Опубликована: Фев. 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.

Язык: 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, Год журнала: 2019, Номер 21(8), С. 2541 - 2545

Опубликована: Апрель 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.

Язык: Английский

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Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

Topics in Current Chemistry, Год журнала: 2018, Номер 376(3)

Опубликована: Апрель 13, 2018

Traditionally employed in the synthesis of small ring systems and rearrangement chemistry, sulfur-based ylides occupy a unique position toolbox synthetic organic chemist. In recent years number pioneering researchers have looked to expand application these unorthodox reagents through use transition metal catalysis. The strength flexibility such combination been shown be key importance developing powerful novel methodologies. This chapter summarises developments metal-catalysed sulfonium/sulfoxonium ylide reactions, as well providing historical perspective. overviewing successes this area, authors hope encourage others into growing field.

Язык: 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, Год журнала: 2018, Номер 360(19), С. 3781 - 3787

Опубликована: Июль 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

Язык: Английский

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