Anderson, Kevin W.
Tundel, Rachel E.
Ikawa, Takashi
Altman, Ryan A.
Buchwald, Stephen L.

Monodentate Phosphines Provide Highly Active Catalysts for Pd-Catalyzed C–N Bond-Forming Reactions of Heteroaromatic Halides/Amines and (H)N-Heterocycles

“,
Angew. Chem. Int. Ed.
,
2006
,
45
(
39
)
,
6523-6527
.
Abstract

Highly reactive catalysts based on palladium and dialkylbiarylphosphino ligands provide unprecedented reactivity and selectivity in C–N bond-forming processes. The bulky monophosphine catalyst system Pd/1 was effective for the reaction of aryl/heteroaryl halides bearing primary amides and 2-aminoheterocycles (see scheme; dba=dibenzylideneacetone, R=CONH2, NH2), thus showing that monodentate phosphines are viable alternatives to, and sometimes superior to, chelating ligands.