Issue 3, 2013

Phosphinimine–borane combinations in frustrated Lewis pair chemistry

Abstract

The phosphinimines Ph3PNR (R = Ph 1, C6F52, tBu 3) are combined with B(C6F5)3 in an effort to explore the frustrated Lewis pair (FLP) chemistry. While compound 1 is shown to form an adduct with the borane, compounds 2 and 3 exhibit no apparent interaction. Nonetheless exposure of each of the three combinations to H2 resulted in the formation of the corresponding salts [Ph3PN(H)R][HB(C6F5)3] (R = Ph 5, C6F56, tBu 7). Reaction of 1 or 2 with B(C6F5)3 and carbon dioxide afforded Ph3PN(R)COOB(C6F5)3 (R = Ph 8, C6F59) while the corresponding reaction with 3 gave rise only to the tBuNCO and (Ph3PO)B(C6F5)3. Reactions of 1–3 and B(C6F5)3 with PhC[triple bond, length as m-dash]CH proceeds to give either deprotonation or addition affording products of the form [Ph3PN(H)R][PhC[triple bond, length as m-dash]CB(C6F5)3] or (Ph3PNR)(Ph)C[double bond, length as m-dash]CH(B(C6F5)3). The factors governing the nature of the dominant products are considered.

Graphical abstract: Phosphinimine–borane combinations in frustrated Lewis pair chemistry

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2012
Accepted
12 Apr 2012
First published
15 May 2012

Dalton Trans., 2013,42, 630-637

Phosphinimine–borane combinations in frustrated Lewis pair chemistry

C. Jiang and D. W. Stephan, Dalton Trans., 2013, 42, 630 DOI: 10.1039/C2DT30720K

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