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Issue 13, 2018
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Formation and reactions of active five-membered phosphane/borane frustrated Lewis pair ring systems

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Abstract

The reactive five-membered frustrated P/B Lewis pair 6a was generated from Tipp-P(vinyl)2 (Tipp: 2,4,6-triisopropylphenyl) by a series of anti-Markovnikov and Markovnikov hydroboration reactions. The in situ generated compound dimerized to give 7a under kinetic control and the dimer pair 8a/9a under thermodynamic control. The Mes*-P(vinyl)2 analogue (Mes*: 2,4,6-tri-tert-butylphenyl) reacts in a similar way, but in this case the thermodynamic dimers are observed at r.t. whereas the monomer 6b is the dominant species at 80 °C in solution. It is an active dihydrogen splitting reagent. The in situ generated monomeric five-membered P/B FLPs undergo addition reactions to various organic π-reagents. With benzaldehyde or phenylacetylene this gave the respective zwitterionic heteronorbornene or -norbornadiene type products, the latter with liberation of ethylene.

Graphical abstract: Formation and reactions of active five-membered phosphane/borane frustrated Lewis pair ring systems

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Publication details

The article was received on 19 Feb 2018, accepted on 21 Feb 2018 and first published on 22 Feb 2018


Article type: Paper
DOI: 10.1039/C8DT00672E
Citation: Dalton Trans., 2018,47, 4449-4454
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    Formation and reactions of active five-membered phosphane/borane frustrated Lewis pair ring systems

    S. Dong, L. Wang, T. Wang, C. G. Daniliuc, M. Brinkkötter, H. Eckert, G. Kehr and G. Erker, Dalton Trans., 2018, 47, 4449
    DOI: 10.1039/C8DT00672E

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