Cross-Coupling of Aryl Halides and Triflates with Intramolecularly Stabilized Group 13-Metal Alkylating Reagents in the Presence of Mixed-Metal Catalysts
The reductive cross coupling of pyridinium salts derived from readily available primary alkyl amines with aryl halides has been achieved under mild reaction conditions using a nickel catalyst.
<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>
Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling