Palladium-catalysed C-F alumination of fluorobenzenes: mechanistic diversity and origin of selectivity.

ABSTRACT: A palladium pre-catalyst, [Pd(PCy₃)₂] is reported for the efficient and selective C-F alumination of fluorobenzenes with the aluminium(i) reagent [{(ArNCMe)₂CH}Al] (1, Ar = 2,6-di-iso-propylphenyl). The catalytic protocol results in the transformation of sp² C-F bonds to sp² C-Al bonds and provides a route to reactive organoaluminium complexes (2a-h) from fluorocarbons. The catalyst is highly active. Reactions proceed within 5 minutes at 25 °C (and at appreciable rates at even -50 °C) and the scope includes low-fluorine-content substrates such as fluorobenzene, difluorobenzenes and trifluorobenzenes. The reaction proceeds with complete chemoselectivity (C-F vs. C-H) and high regioselectivities (>90% for C-F bonds a

SUBMITTER: Rekhroukh F 

PROVIDER: S-EPMC8163258 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature