Pd-catalyzed Suzuki synth of phenylacetamides

[Rhodium]

This could be a novel route to phenethylamines. Formation of the boronic ester from an aryl halide, running this coupling reaction and then reduce with LAH or NaBH4/H2SO4.

Abstract

A Suzuki-type cross-coupling of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide in the presence of a catalytic amount of tricyclohexylphosphine as the ligand and hydroquinone as the free-radical scavenger has been demonstrated as a convenient and simple way for the synthesis of alpha-arylacetamides.

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Reference:

Tetrahedron Letters Volume 44, Issue 8, Pages 1587-1590 (2003)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pd.arylacetamide.pdf)