A Unified and Practical Method for Carbon-Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis

While carbon-heteroatom cross-coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C-O, C-N and C-S cross-coupling reactions under one general set of conditions. 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 bromides, iodides, and chlorides to 1 degrees and 2 degrees alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.