Diverse Reactivity of an Al(I)-centred Anion Towards Ketones

Michael Hill; Han-Ying Dennis Liu; Mary Mahon

doi:10.1039/D2CC02333D

Diverse Reactivity of an Al(I)-centred Anion Towards Ketones

Michael Hill, Han-Ying Dennis Liu, Mary Mahon

Research output: Contribution to journal › Article › peer-review

10 Citations (SciVal)

Abstract

The reactivity of a seven-membered cyclic potassium diamidoalumanyl toward a variety of ketone small molecules has been assessed. Whilst acetophenone generates an aluminium pinacolate derivative, reductive C-C coupling is induced between the ketyl and ortho-carbon centres of two equivalents of benzophenone. In contrast, whereas oxidative addition of an enolisable proton is observed with 2,4-dimethyl-3-pentanone, 2,2,4,4-tetramethyl-3-pentanone undergoes an unprecedented hydroalumination process, where the reducing hydride may be traced to intramolecular oxidative addition of a (sp3)C-H bond.

Original language	English
Pages (from-to)	6938-6941
Number of pages	4
Journal	Chemical communications (Cambridge, England)
Volume	58
Issue number	49
Early online date	24 May 2022
DOIs	https://doi.org/10.1039/D2CC02333D
Publication status	Published - 24 May 2022

Bibliographical note

We thank the EPSRC (UK) for their generous support of this research (EP/R020752/1).

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/D2CC02333DLicence: CC BY

Cite this

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abstract = "The reactivity of a seven-membered cyclic potassium diamidoalumanyl toward a variety of ketone small molecules has been assessed. Whilst acetophenone generates an aluminium pinacolate derivative, reductive C-C coupling is induced between the ketyl and ortho-carbon centres of two equivalents of benzophenone. In contrast, whereas oxidative addition of an enolisable proton is observed with 2,4-dimethyl-3-pentanone, 2,2,4,4-tetramethyl-3-pentanone undergoes an unprecedented hydroalumination process, where the reducing hydride may be traced to intramolecular oxidative addition of a (sp3)C-H bond.",

author = "Michael Hill and Liu, {Han-Ying Dennis} and Mary Mahon",

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AU - Hill, Michael

AU - Liu, Han-Ying Dennis

AU - Mahon, Mary

N1 - We thank the EPSRC (UK) for their generous support of this research (EP/R020752/1).

PY - 2022/5/24

Y1 - 2022/5/24

N2 - The reactivity of a seven-membered cyclic potassium diamidoalumanyl toward a variety of ketone small molecules has been assessed. Whilst acetophenone generates an aluminium pinacolate derivative, reductive C-C coupling is induced between the ketyl and ortho-carbon centres of two equivalents of benzophenone. In contrast, whereas oxidative addition of an enolisable proton is observed with 2,4-dimethyl-3-pentanone, 2,2,4,4-tetramethyl-3-pentanone undergoes an unprecedented hydroalumination process, where the reducing hydride may be traced to intramolecular oxidative addition of a (sp3)C-H bond.

AB - The reactivity of a seven-membered cyclic potassium diamidoalumanyl toward a variety of ketone small molecules has been assessed. Whilst acetophenone generates an aluminium pinacolate derivative, reductive C-C coupling is induced between the ketyl and ortho-carbon centres of two equivalents of benzophenone. In contrast, whereas oxidative addition of an enolisable proton is observed with 2,4-dimethyl-3-pentanone, 2,2,4,4-tetramethyl-3-pentanone undergoes an unprecedented hydroalumination process, where the reducing hydride may be traced to intramolecular oxidative addition of a (sp3)C-H bond.

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JO - Chemical communications (Cambridge, England)

JF - Chemical communications (Cambridge, England)

IS - 49

ER -

Diverse Reactivity of an Al(I)-centred Anion Towards Ketones

Abstract

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Nucleophilic alkaline earth boryls: from conception and theory to application

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Diverse Reactivity of an Al(I)-centred Anion Towards Ketones

Abstract

Bibliographical note

ASJC Scopus subject areas

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Nucleophilic alkaline earth boryls: from conception and theory to application

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