Jump to Main Content
Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair
- Mehta, Meera, Goicoechea, Jose M.
- Chemical communications 2019 v.55 no.48 pp. 6918-6921
- aluminum, dimerization, heterocyclic compounds, moieties
- We report on the reactivity of isocyanates towards tris(pentafluorophenyl)borane which was found to result in the 1,2-carboboration of the isocyanate CO bond. The resulting six-membered heterocyclic compounds can be rationalized as adducts of imino-boranes with isocyanates and react accordingly, allowing for the dissociative displacement of the trapped isocyanate moiety in a series of exchange reactions. Related carboelementation reactions with the heavier group 13 analogues, Al(C₆F₅)₃ and Ga(C₆F₅)₃, result in a dimerization of the carboboration products to afford eight-membered heterocycles.