A Ni/1-bpp catalyst was demonstrated to be effective
in the Negishi
alkylation with multiple classes of alkylpyridinium salts, including
α-primary and α-secondary. These conditions are also effective
for benzylic pyridinium salts, demonstrating the successful Negishi
alkylation of benzylic pyridinium salts for the first time. Further,
14 derivatives of 1-bpp were prepared with a variety of steric and
electronic properties to study how these changes impact the success
of the Negishi alkylation.