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Issue 32, 2010
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Addition reactions to the intramolecular mesityl2P–CH2–CH2–B(C6F5)2 frustrated Lewis pair

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Abstract

Hydroboration of dimesitylvinylphosphine with Piers’ borane [HB(C6F5)2] gives the ethylene-bridged intramolecular frustrated P/B Lewis pair 1. It adds pyridine, tert-butyl isocyanide or pivalonitrile to the strongly electrophilic boron center to yield the respective adducts 5–7. Compound 1 undergoes a 1,1-phosphine/borane addition to the terminal nitrogen center of phenyl azide to yield the five-membered heterocycle 8, featuring a pendant –N[double bond, length as m-dash]N–Ph. This can be regarded as a boron-stabilized intermediate of a Staudinger reaction. Benzaldehyde and phenyl isocyanate undergo 1,2-P/B additions of 1 to their reactive carbonyl groups to yield the corresponding six-membered heterocycles 9 and 10, respectively. The P/B Lewis pair reacts with nitrosobenzene by 1,2-addition to the –N[double bond, length as m-dash]O unit under P–N and O–B bond formation to give the six-membered heterocycle 11. The compounds 511 were characterized by X-ray crystal structure analyses.

Graphical abstract: Addition reactions to the intramolecular mesityl2P–CH2–CH2–B(C6F5)2 frustrated Lewis pair

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Publication details

The article was received on 22 Feb 2010, accepted on 06 May 2010 and first published on 08 Jul 2010


Article type: Paper
DOI: 10.1039/C0DT00015A
Dalton Trans., 2010,39, 7556-7564

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    Addition reactions to the intramolecular mesityl2P–CH2–CH2–B(C6F5)2 frustrated Lewis pair

    C. M. Mömming, G. Kehr, B. Wibbeling, R. Fröhlich and G. Erker, Dalton Trans., 2010, 39, 7556
    DOI: 10.1039/C0DT00015A

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