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Issue 16, 2020
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The phosphinoboration of acyl chlorides

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Abstract

This investigation examines the reactivity of phosphinoboronate esters Ph2PBpin (pin = 1,2-O2C2Me4) and Ph2PBcat (cat = 1,2-O2C6H4), as well as other phosphinoboron species, with various aryl and aliphatic acyl chlorides. These reactions proceed smoothly to give acyl phosphines of the type RC(O)PR′2 along with loss of a boron-chloride compound. In some cases, a second equivalent of the phosphinoboron species can add to the C[double bond, length as m-dash]O double bond at elevated temperatures to give the corresponding diphosphines RC(OBR′′2)(PR′2)2. These ambiphilic diphosphines behave like substituted (1,1-bis(diphenylphosphino)methane) derivatives in a reaction of PhC(OBpin)(PPh2)2 (2a) with (η5-C9H7)Rh(η2-coe)2 (coe = cis-cyclooctene) affording the indenyl rhodium complex (η5-C9H7)Rh(PhC(OBpin)(PPh2)2) (3a) where the phosphines are bound to the metal centre in a κ2-P,P bidentate manner.

Graphical abstract: The phosphinoboration of acyl chlorides

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Supplementary files

Article information


Submitted
16 Feb 2020
Accepted
05 Mar 2020
First published
06 Mar 2020

Dalton Trans., 2020,49, 5092-5099
Article type
Paper

The phosphinoboration of acyl chlorides

M. C. Murphy, A. Trofimova, J. H. W. LaFortune, C. M. Vogels, S. J. Geier, J. F. Binder, C. L. B. Macdonald, D. W. Stephan and S. A. Westcott, Dalton Trans., 2020, 49, 5092
DOI: 10.1039/D0DT00579G

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