Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific andlimited 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.