Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents

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Abstract: The use of arylboron reagents in metal‐catalyzed domino addition–cyclization reactions is a well‐established strategy for the preparation of diverse, highly functionalized carbo‐ and heterocyclic products. Although rhodium‐ and palladium‐based catalysts have been commonly used for these reactions, more recent work has demonstrated nickel catalysis is also highly effective, in many cases offering unique reactivity and access to products that might otherwise not be readily available. This review gives an overview of nickel‐catalyzed arylative cyclizations of alkyne‐ and allene‐tethered electrophiles using arylboron reagents. The scope of the reactions is discussed in detail, and general mechanistic concepts underpinning the processes are described.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents ; day:27 ; month:01 ; year:2022 ; extent:1
Chemistry - a European journal ; (27.01.2022) (gesamt 1)

Creator: Gillbard, Simone M.
Lam, Hon Wai

DOI: 10.1002/chem.202104230

URN: urn:nbn:de:101:1-2022012814123607636700

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:33 AM CEST

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Gillbard, Simone M.
Lam, Hon Wai

Other Objects (12)

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Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones

Nickel-catalyzed acylzincation of allenes with organozincs and CO

Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Dynamic Kinetic Resolution Strategy for the Asymmetric Nickel-Catalyzed Capture of Transient Cyclic Allenes

Intramolecular Carboxyamidation of Alkyne‐Tethered O ‐Acylhydroxamates through Formation of Fe (III)‐Nitrenoids

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Cycloisomerization of Alkyne‐Tethered N ‐Acyloxycarbamates to 2‐(3H) Oxazolones through Nitrenoid‐Mediated Carboxyamidation

Catalytic 1,3‐H Atom Shift of a Terminal Benzylic Alkyne by Iron and Alkali Metal Silylamides – Switching between Allene and Internal Alkyne

DFT Mechanistic Insights into the Ni (II)‐Catalyzed Enantioselective Arylative Cyclization of Tethered Allene‐Ketones

Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions

Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones

Nickel-catalyzed acylzincation of allenes with organozincs and CO

Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Dynamic Kinetic Resolution Strategy for the Asymmetric Nickel-Catalyzed Capture of Transient Cyclic Allenes

Intramolecular Carboxyamidation of Alkyne‐Tethered O ‐Acylhydroxamates through Formation of Fe (III)‐Nitrenoids

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Cycloisomerization of Alkyne‐Tethered N ‐Acyloxycarbamates to 2‐(3H) Oxazolones through Nitrenoid‐Mediated Carboxyamidation

Catalytic 1,3‐H Atom Shift of a Terminal Benzylic Alkyne by Iron and Alkali Metal Silylamides – Switching between Allene and Internal Alkyne

DFT Mechanistic Insights into the Ni (II)‐Catalyzed Enantioselective Arylative Cyclization of Tethered Allene‐Ketones

Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions

Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones

Nickel-catalyzed acylzincation of allenes with organozincs and CO

Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Dynamic Kinetic Resolution Strategy for the Asymmetric Nickel-Catalyzed Capture of Transient Cyclic Allenes

Intramolecular Carboxyamidation of Alkyne‐Tethered O ‐Acylhydroxamates through Formation of Fe (III)‐Nitrenoids

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Cycloisomerization of Alkyne‐Tethered N ‐Acyloxycarbamates to 2‐(3H) Oxazolones through Nitrenoid‐Mediated Carboxyamidation

Catalytic 1,3‐H Atom Shift of a Terminal Benzylic Alkyne by Iron and Alkali Metal Silylamides – Switching between Allene and Internal Alkyne

DFT Mechanistic Insights into the Ni (II)‐Catalyzed Enantioselective Arylative Cyclization of Tethered Allene‐Ketones

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Nickel‐Catalyzed Arylative Cyclizations of Alkyne‐ and Allene‐Tethered Electrophiles using Arylboron Reagents

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Other Objects (12)

Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions

Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones

Nickel-catalyzed acylzincation of allenes with organozincs and CO

Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Dynamic Kinetic Resolution Strategy for the Asymmetric Nickel-Catalyzed Capture of Transient Cyclic Allenes

Intramolecular Carboxyamidation of Alkyne‐Tethered O ‐Acylhydroxamates through Formation of Fe (III)‐Nitrenoids

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Cycloisomerization of Alkyne‐Tethered N ‐Acyloxycarbamates to 2‐(3H) Oxazolones through Nitrenoid‐Mediated Carboxyamidation

Catalytic 1,3‐H Atom Shift of a Terminal Benzylic Alkyne by Iron and Alkali Metal Silylamides – Switching between Allene and Internal Alkyne

DFT Mechanistic Insights into the Ni (II)‐Catalyzed Enantioselective Arylative Cyclization of Tethered Allene‐Ketones

Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions

Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones

Nickel-catalyzed acylzincation of allenes with organozincs and CO

Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Dynamic Kinetic Resolution Strategy for the Asymmetric Nickel-Catalyzed Capture of Transient Cyclic Allenes

Intramolecular Carboxyamidation of Alkyne‐Tethered O ‐Acylhydroxamates through Formation of Fe (III)‐Nitrenoids

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Cycloisomerization of Alkyne‐Tethered N ‐Acyloxycarbamates to 2‐(3H) Oxazolones through Nitrenoid‐Mediated Carboxyamidation

Catalytic 1,3‐H Atom Shift of a Terminal Benzylic Alkyne by Iron and Alkali Metal Silylamides – Switching between Allene and Internal Alkyne

DFT Mechanistic Insights into the Ni (II)‐Catalyzed Enantioselective Arylative Cyclization of Tethered Allene‐Ketones

Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions

Enantioselective Nickel‐Catalyzed anti ‐Arylmetallative Cyclizations onto Acyclic Ketones

Nickel-catalyzed acylzincation of allenes with organozincs and CO

Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling

Spirocyclization of Alkyne-Tethered Aromatics with Silver Nitrate/Silica

Dynamic Kinetic Resolution Strategy for the Asymmetric Nickel-Catalyzed Capture of Transient Cyclic Allenes

Intramolecular Carboxyamidation of Alkyne‐Tethered O ‐Acylhydroxamates through Formation of Fe (III)‐Nitrenoids

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Cycloisomerization of Alkyne‐Tethered N ‐Acyloxycarbamates to 2‐(3H) Oxazolones through Nitrenoid‐Mediated Carboxyamidation

Catalytic 1,3‐H Atom Shift of a Terminal Benzylic Alkyne by Iron and Alkali Metal Silylamides – Switching between Allene and Internal Alkyne

DFT Mechanistic Insights into the Ni (II)‐Catalyzed Enantioselective Arylative Cyclization of Tethered Allene‐Ketones

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