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Issue 31, 2007
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Tuning Lewis acidity using the reactivity of “frustrated Lewis pairs”: facile formation of phosphine-boranes and cationic phosphonium-boranes

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Abstract

The concept of “frustrated Lewis pairs” involves donor and acceptor sites in which steric congestion precludes Lewis acid–base adduct formation. In the case of sterically demanding phosphines and boranes, this lack of self-quenching prompts nucleophilic attack at a carbon para to B followed by fluoride transfer affording zwitterionic phosphonium borates [R3P(C6F4)BF(C6F5)2] and [R2PH(C6F4)BF(C6F5)2]. These can be easily transformed into the cationic phosphonium-boranes [R3P(C6F4)B(C6F5)2]+ and [R2PH(C6F4)B(C6F5)2]+ or into the neutral phosphino-boranes R2P(C6F4)B(C6F5)2. This new reactivity provides a modular route to a family of boranes in which the steric features about the Lewis acidic center remains constant and yet the variation in substitution provides a facile avenue for the tuning of the Lewis acidity. Employing the Gutmann–Beckett and Childs methods for determining Lewis acid strength, it is demonstrated that the cationic boranes are much more Lewis acidic than B(C6F5)3, while the acidity of the phosphine-boranes is diminished.

Graphical abstract: Tuning Lewis acidity using the reactivity of “frustrated Lewis pairs”: facile formation of phosphine-boranes and cationic phosphonium-boranes

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Article information


Submitted
22 Mar 2007
Accepted
02 May 2007
First published
17 May 2007

Dalton Trans., 2007, 3407-3414
Article type
Paper

Tuning Lewis acidity using the reactivity of “frustrated Lewis pairs”: facile formation of phosphine-boranes and cationic phosphonium-boranes

G. C. Welch, L. Cabrera, P. A. Chase, E. Hollink, J. D. Masuda, P. Wei and D. W. Stephan, Dalton Trans., 2007, 3407
DOI: 10.1039/B704417H

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