Palladium-Catalysed Carbon-Fluorine and Carbon-Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes

DOI: 10.14469/hpc/2663 Metadata

Created: 2017-06-15 10:23

Last modified: 2017-08-15 10:18

Author: Tom Hooper

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Co-author: Andrew White
Co-author: Mark Crimmin


Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp2C–F and sp2C–H bonds of fluoroarenes and heteroarenes to sp2C–Al bonds (19 examples, 1 mol% Pd loading). The carbon–fluorine bond functionalization reaction is highly selec-tive for the formation of organoaluminum products in preference to hydrodefluorination products (selectivity = 4.4:1 to 27:1). Evidence is presented for a two step mechanism in which hydrodefluorination is followed by sp2C–H alumination.


10.14469/hpc/2664 Compound 3m
10.14469/hpc/2665 Compound 3n
10.14469/hpc/2666 Compound 3o
10.14469/hpc/2667 Compound 3p
10.14469/hpc/2668 Compound 3q
10.14469/hpc/2669 Compound 3r
10.14469/hpc/2670 Compound 3s
10.14469/hpc/2671 Compound 3t
10.14469/hpc/2672 Compound 3l
10.14469/hpc/2673 Compound 3k
10.14469/hpc/2674 Substrate NMR