Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 26, 2024

Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp

Язык: Английский

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Nickel(0)‐Catalyzed Hydroarylation of Styrenes and 1,3‐Dienes with Organoboron Compounds

Angewandte Chemie International Edition, Год журнала: 2017, Номер 57(2), С. 461 - 464

Опубликована: Ноя. 21, 2017

Abstract A Ni‐catalyzed hydroarylation of styrenes and 1,3‐dienes with organoboron compounds has been developed. The reaction offers a highly selective approach to diarylalkanes allylarenes under redox‐neutral conditions. In this reaction, new strategy that uses the proton methanol generate active catalyst species Ni−H was hydroarylation, combined Ir‐catalyzed C−H borylation, affords very efficient straightforward access retinoic acid receptor agonist.

Язык: Английский

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Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling

ACS Catalysis, Год журнала: 2018, Номер 8(10), С. 9245 - 9251

Опубликована: Сен. 4, 2018

In this protocol, we report an allylic defluorinative reductive cross-coupling reaction for C–C bond formation. Under the Ni-catalysis challenging C(sp3)–F cleavage of trifluoromethyl-substituted alkenes was achieved with easily accessible primary, secondary and tertiary alkyl halides as coupling partners Zn-powder reducing agent. This process provides efficient convenient entry to gem-difluoroalkenes bearing various sensitive functional groups under mild conditions. Moreover, method proves be suitable late-stage functionalization multifunctional complex molecules.

Язык: Английский

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Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols

Nature Communications, Год журнала: 2019, Номер 10(1)

Опубликована: Апрель 15, 2019

Abstract Direct (utilize easily available and abundant precursors) selective (both chemo- regio-) aliphatic C–H functionalization is an attractive mean with which to streamline chemical synthesis. With many possible sites of reaction, traditional methods often need adjacent polar directing group nearby achieve high regio- chemoselectivity are restricted a single site functionalization. Here we report remote thiolation process predictable switchable regioselectivity through NiH-catalysed migratory hydrothiolation two feedstock chemicals (alkenes/alkynes thiols). This mild reaction avoids the preparation electrophilic reagents highly thiols over other nucleophilic groups, such as alcohols, acids, amines, amides. Mechanistic studies show that occurs formation RS-Bpin intermediate, THF solvent plays important role in regeneration NiH species.

Язык: Английский

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Ligand-Controlled Nickel-Catalyzed Reductive Relay Cross-Coupling of Alkyl Bromides and Aryl Bromides

ACS Catalysis, Год журнала: 2017, Номер 8(1), С. 310 - 313

Опубликована: Дек. 1, 2017

1,1-Diarylalkanes are important structural frameworks which widespread in biologically active molecules. Herein, we report a reductive relay cross-coupling of alkyl bromides with aryl by nickel catalysis simple nitrogen-containing ligand. This method selectively affords 1,1-diarylalkane derivatives good to excellent yields and regioselectivity.

Язык: Английский

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