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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
Reactivity of B ← P coordinated phosphide with isocyanides: bases or nucleophiles?
Michal Aman1, Tomáš Bíza1, Libor Dostál1
1Department of General and Inorganic Chemistry, University of Pardubice, 532 10 Pardubice, Czech Republic. roman.jambor@upce.cz.
Abstract:
The reactivity of the sodium phosphido-borane complex, [Na(THF)3]+[1-BCy2-8-PPh-C10H6]- (1), with RCH2NC isocyanides is reported. In contrast to traditional bases or phosphides, 1 act as an efficient nucleophile to form reactive carbanion intermediates instead of proton abstraction from RCH2NC and formation of protonated phoshane 1-BCy2-8-P(H)Ph-C10H6 (2). This study showed that 1 acts as a nucleophile and reacts with RCH2NC in a 1 : 2 stoichiometry to form a 2-imidazoline, imidazole or an enamine. Isolated compounds demonstrate the ability of 1 in promoting carbanion formation and participating in subsequent reactions to give various N-substituted alkyl phosphine organic compounds, which are not usually obtained by different synthetical approaches.
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