Reactivity of B ← P coordinated phosphide with isocyanides: bases or nucleophiles?

Authors

Michal Aman, Tomáš Bíza, Libor Dostál, Zdeňka Růžičková, Emanuel Hupf, Roman Jambor

Published in

Dalton transactions (Cambridge, England : 2003). Sep 30, 2026. Epub Sep 30, 2026.

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.

PMID:
42814504
Bibliographic data and abstract were imported from PubMed on 01 Oct 2026.

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