Issue 13, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Feb 2018
Accepted
21 Feb 2018
First published
22 Feb 2018

Dalton Trans., 2018,47, 4449-4454

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements