1612891-27-6Relevant articles and documents
Room-temperature amination of deactivated aniline and aryl halide partners with carbonate base using a Pd-PEPPSI-IPentCl-o-picoline catalyst
Pompeo, Matthew,Farmer, Jennifer L.,Froese, Robert D. J.,Organ, Michael G.
supporting information, p. 3223 - 3226 (2014/04/03)
Current state-of-the-art protocols for the coupling of unreactive amines (e.g., electron-poor anilines) with deactivated oxidative-addition partners (e.g., electron-rich and/or hindered aryl chlorides) involve strong heating (usually >100 °C) and/or tert-butoxide base, and even then not all couplings are successful. The aggressive base tert-butoxide reacts with and in many instances destroys the typical functional groups that are necessary for the function of most organic molecules, such as carbonyl groups, esters, nitriles, amides, alcohols, and amines. The new catalyst described herein, Pd-PEPPSI-IPentCl-o-picoline, is able to aminate profoundly deactivated coupling partners when using only carbonate base at room temperature. Running mild: An N-heterocyclic carbene complex of palladium (1) was systematically designed to enable the amination of strongly deactivated substrates (R1 can be strongly electron donating, R2 can be strongly electron-withdrawing) when using the most mild of bases (carbonate) at room temperature. This catalyst was used to produce elaborate, richly functionalized products for use in life-, health-, and material-science applications.