879329-56-3Relevant articles and documents
Reactions of Fluoroalkenes with an Aluminium(I) Complex
Bakewell, Clare,White, Andrew J. P.,Crimmin, Mark R.
, p. 6638 - 6642 (2018)
A series of industrially relevant fluoroalkenes react with a monomeric AlI complex. These reactions break strong sp2 and sp3 C?F bonds, and result in the formation of a diverse array of organoaluminium compounds. Mechanistic studies show that two mechanisms are likely in operation: 1) direct oxidative addition of the C?F bond to AlI occurs with retention of alkene stereochemistry, and 2) stepwise formation and decomposition of a metallocyclopropane intermediate occurs with inversion of alkene stereochemistry. As part of this mechanistic analysis, we have isolated the first aluminium metallocyclopropane complex from oxidative addition of an alkene to AlI. Remarkably this reaction is reversible and reductive elimination of the alkene occurs at higher temperature reforming AlI. Furthermore, in selected cases the organoaluminium products are susceptible toward β-fluoride elimination to yield a double C?F activation pathway.
