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C[double bond, length as m-dash]O scission and reductive coupling of organic carbonyls by a redox-active diboraanthracene

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Abstract

The boron-centered reactivity of the diboraanthracene-auride complex [Au(B2P2)][K(18-c-6)]; (B2P2, 9,10-bis(2-(diisopropylphosphino)-phenyl)-9,10-dihydroboranthrene) with a series of organic carbonyls is reported. The reaction of [Au(B2P2)] with formaldehyde or paraformaldehyde results in a head-to-tail dimerization of two formaldehyde units across the boron centers. In contrast, the reaction of [(B2P2)Au] with two equivalents of benzaldehyde yields the pinacol coupling product via C–C bond formation. Careful stoichiometric addition of one equivalent of benzaldehyde to [Au(B2P2)] enabled the isolation of an adduct corresponding to the formal [4+2] cycloaddition of the C[double bond, length as m-dash]O bond of benzaldehyde across the boron centers. This adduct reacts with a second equivalent of benzaldehyde to produce the pinacol coupling product. Finally, the reaction of [Au(B2P2)] with acetone results in a formal reductive deoxygenation with discrete hydroxo and 2-propenyl units bound to the boron centers. This reaction is proposed to proceed via an analogous [4+2] cycloadduct, highlighting the unique small molecule activation chemistry available to this platform.

Graphical abstract: C [[double bond, length as m-dash]] O scission and reductive coupling of organic carbonyls by a redox-active diboraanthracene

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Article information


Submitted
12 Feb 2020
Accepted
06 Mar 2020
First published
09 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

C[double bond, length as m-dash]O scission and reductive coupling of organic carbonyls by a redox-active diboraanthracene

J. W. Taylor and W. H. Harman, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01142H

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