Issue 16, 2020

The phosphinoboration of acyl chlorides

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

Supplementary files

Article information

Article type
Paper
Submitted
16 feb 2020
Accepted
05 mar 2020
First published
06 mar 2020

Dalton Trans., 2020,49, 5092-5099

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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