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

Dalton Transactions : an International Journal of Inorganic Chemistry
Shunxi DongGerhard Erker

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.

References

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Citations

Oct 26, 2018·Chemical Communications : Chem Comm·Jun LiGerhard Erker
Jan 22, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Alexander A MalärThomas Wiegand
Mar 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Robert KnitschHellmut Eckert
Jul 7, 2020·Chemical Communications : Chem Comm·Chaohuang ChenGerhard Erker
Feb 19, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Qiu SunGerhard Erker
Oct 2, 2021·Angewandte Chemie·Jun LiGerhard Erker

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Methods Mentioned

BETA
X-ray
NMR

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