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Literature DB >> 22414150

Nickel-catalyzed Negishi alkylations of styrenyl aziridines.

Abstract

A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C bond formation.

Entities: Chemical

Year: 2012 PMID： 22414150 DOI： 10.1021/ja3013825

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

29 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

2. Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer.

Authors: David N Primer; Gary A Molander
Journal: J Am Chem Soc Date: 2017-07-18 Impact factor: 15.419

3. Nickel Catalysis: Synergy between Method Development and Total Synthesis.

Authors: Eric A Standley; Sarah Z Tasker; Kim L Jensen; Timothy F Jamison
Journal: Acc Chem Res Date: 2015-04-23 Impact factor: 22.384

4. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors: Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal: ACS Catal Date: 2020-09-10 Impact factor: 13.084

5. Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.

Authors: Talia J Steiman; Junyi Liu; Amanuella Mengiste; Abigail G Doyle
Journal: J Am Chem Soc Date: 2020-04-06 Impact factor: 15.419

Nickel-catalyzed Negishi alkylations of styrenyl aziridines.

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

2. Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer.

3. Nickel Catalysis: Synergy between Method Development and Total Synthesis.

4. Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

5. Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.

6. Nitric oxide activation by distal redox modulation in tetranuclear iron nitrosyl complexes.

7. Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons.

8. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

9. Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

10. Multicomponent assembly of highly substituted indoles by dual palladium-catalyzed coupling reactions.