3d Transition Metals for C–H Activation

Chemical Reviews, Год журнала: 2018, Номер 119(4), С. 2192 - 2452

Опубликована: Ноя. 27, 2018

C–H activation has surfaced as an increasingly powerful tool for molecular sciences, with notable applications to material crop protection, drug discovery, and pharmaceutical industries, among others. Despite major advances, the vast majority of these functionalizations required precious 4d or 5d transition metal catalysts. Given cost-effective sustainable nature earth-abundant first row metals, development less toxic, inexpensive 3d catalysts gained considerable recent momentum a significantly more environmentally-benign economically-attractive alternative. Herein, we provide comprehensive overview on until summer 2018.

Язык: Английский

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Dehydrogenative Coupling of Benzylic and Aldehydic C–H Bonds

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(7), С. 3366 - 3370

Опубликована: Фев. 3, 2020

A photoinduced dehydrogenative coupling reaction between benzylic and aldehydic C–H bonds is reported. When a solution of an alkylbenzene aldehyde in ethyl acetate irradiated with visible light the presence iridium nickel catalysts, coupled α-aryl ketone formed evolution dihydrogen. An analogous C–C bond forming occurs next to nitrogen N-methylamide produce α-amino ketone. These reactions provide straightforward pathway from readily available materials leading valued structural motifs pharmacological relevance.

Язык: Английский

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Cobalt‐Catalyzed Annulation Reactions via C−H Bond Activation

ChemCatChem, Год журнала: 2017, Номер 10(4), С. 683 - 705

Опубликована: Ноя. 1, 2017

Abstract Considerable research attention has been directed towards the use of first‐row transition metals in organic synthesis. The more abundant, and less expensive cobalt is considered to be an effective alternative for second third‐row noble metals, especially C−H bond functionalization reactions. In this Minireview, we will summarize features, recent achievements Co‐catalyzed directing group assisted activation/cyclization reactions their mechanistic insights.

Язык: Английский

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Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

Asian Journal of Organic Chemistry, Год журнала: 2019, Номер 8(11), С. 1949 - 1969

Опубликована: Март 13, 2019

Abstract Maleimide and succinimide core moieties are present in various natural products pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines γ‐lactams. A transition‐metal‐catalyzed chelation‐assisted functionalization of inert C−H bond with electrophiles or nucleophiles is one the efficient methods to construct chemical bonds a highly atom‐ step‐economical manner. The review describes recent advances reaction involving maleimides by activation methodology. having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N ‐sulfonyl ketimine, carboxylic acids, aldimines, were described. scope, limitation mechanistic investigation alkylation, annulation alkenylation reactions discussed elaborately. This article includes entire report on bond‐forming strategy until end 2018.

Язык: Английский

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Recent advances in cobalt-catalysed C–H functionalizations

Organic & Biomolecular Chemistry, Год журнала: 2019, Номер 17(48), С. 10119 - 10141

Опубликована: Янв. 1, 2019

Ready availability, low cost and toxicity of cobalt salts have redirected the attention researchers away from noble metals, such as Pd, Rh, Ir, towards Co in field C-H functionalization. In this context, examples Co-catalysed functionalization exponentially grown over last few decades. This present review focuses on most recent developments C(sp2)-H C(sp3)-H functionalizations. Included is also a comprehensive overview enantioselective transformations.

Язык: Английский

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Synthesis of Fused or Spiro Polyheterocyclic Compounds via the Dehydrogenative Annulation Reactions of 2-Arylindazoles with Maleimides

Organic Letters, Год журнала: 2019, Номер 21(18), С. 7189 - 7193

Опубликована: Сен. 4, 2019

A dehydrogenative annulation of 2-arylindazoles with maleimides for the switchable synthesis indazolo[2,3-a]pyrrolo[3,4-c]quinolinones or spiroindolo[1,2-b]indazole-11,3′-pyrrolidinones is presented. Mechanistically, formation title compounds involves a Rh(III)-catalyzed C–H metalation 2-arylindazole, followed by maleimide insertion and intramolecular cyclization. Interestingly, selectivity to form fused spiro could be switched resorting different additives. The notable features this protocol include simple substrates excellent atom economy regioselectivity.

Язык: Английский

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Cobalt-catalyzed C–H activation: recent progress in heterocyclic chemistry

Catalysis Science & Technology, Год журнала: 2018, Номер 8(23), С. 5983 - 6018

Опубликована: Янв. 1, 2018

Cobalt-catalyzed C–H activation has gone through some major advancements in the past couple of decades.

Язык: Английский

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Cobalt-Catalyzed Oxidative Cyclization of Benzamides with Maleimides: Synthesis of Isoindolone Spirosuccinimides

Organic Letters, Год журнала: 2017, Номер 19(21), С. 5884 - 5887

Опубликована: Окт. 18, 2017

The oxidative cyclization of substituted benzamides with maleimides assisted by 8-aminoquinoline in the presence a catalytic amount Co(OAc)2·4H2O provides isoindolone spirosuccinimides good to excellent yields. reaction was compatible various and maleimides. A possible mechanism involving C-H bond activation as key step proposed. competition experiment deuterium labeling studies were performed investigate reaction.

Язык: Английский

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

Organic Letters, Год журнала: 2018, Номер 20(18), С. 5981 - 5984

Опубликована: Сен. 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.

Язык: Английский

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Transition metal-catalyzed coupling of heterocyclic alkenesviaC–H functionalization: recent trends and applications

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(12), С. 1527 - 1569

Опубликована: Янв. 1, 2020

Heterocyclic alkenes and their derivatives are an important class of reactive feedstock valuable synthons. This review highlights the transition-metal-catalyzed coupling heterocyclic alkenesviaa C–H functionalization strategy.

Язык: Английский

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