Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN2  Pincer Ligand Complex

Thomas L Andersen; Aske S Donslund; Karoline T Neumann; Troels Skrydstrup

doi:10.1002/anie.201710089

Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN₂ Pincer Ligand Complex

Thomas L Andersen, Aske S Donslund, Karoline T Neumann, Troels Skrydstrup

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

90 Citations (Scopus)

Abstract

An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp3 -carbon fragments. The method, which relies on the application of nickel complexed with an NN2 -type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	57
Issue	3
Pages (from-to)	800-804
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201710089
Publication status	Published - 2018

Keywords

Journal Article

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title = "Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN2 Pincer Ligand Complex",

abstract = "An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp3 -carbon fragments. The method, which relies on the application of nickel complexed with an NN2 -type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.",

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author = "Andersen, {Thomas L} and Donslund, {Aske S} and Neumann, {Karoline T} and Troels Skrydstrup",

note = "{\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2018",

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journal = "Angewandte Chemie International Edition",

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Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN₂ Pincer Ligand Complex. / Andersen, Thomas L; Donslund, Aske S; Neumann, Karoline T et al.
In: Angewandte Chemie International Edition, Vol. 57, No. 3, 2018, p. 800-804.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

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T1 - Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN2 Pincer Ligand Complex

AU - Andersen, Thomas L

AU - Donslund, Aske S

AU - Neumann, Karoline T

AU - Skrydstrup, Troels

PY - 2018

Y1 - 2018

N2 - An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp3 -carbon fragments. The method, which relies on the application of nickel complexed with an NN2 -type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.

AB - An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp3 -carbon fragments. The method, which relies on the application of nickel complexed with an NN2 -type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.

KW - Journal Article

U2 - 10.1002/anie.201710089

DO - 10.1002/anie.201710089

M3 - Journal article

C2 - 29193522

SN - 1433-7851

VL - 57

SP - 800

EP - 804

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

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