Individuation and study of supported catalytic systems suitable for practically useful C-C cross-coupling reactions performed in batch and/or flow conditions

Abstract

In the context of organic chemistry, and in particular in the C-C cross-coupling reactions catalyzed by transition metals such as nickel or palladium, the use of green and environmental friendly synthetic methodologies is of growing interest for both Academy and Industry. In this context, the replacement of homogeneous metal catalysts with heterogeneous systems and the replacement of classical batch-type reactors with continuous flow systems is today considered of primary importance. Our investigations demonstrated that under rather simple and convenient conditions (a moderate excess of bases, a moderate amount of organic solvents, or in some cases, in only water or in absence of solvents, under aerobic atmosphere and with very low metals loading (0.10-0.15 mol% of Pd); cheap, simple, practical, easily available and industrially acceptable supported catalysts (“purpose-build” and/or commercial), and continuous-flow packed-bed systems, could be conveniently applied in C-C bond forming reactions of particular interest, such as Mizoroki-Heck alkenylations, Sonogashira-type alkynylations and Suzuki-Miyaura reactions; obtaining very good results. Moreover, we reported the application of these systems in one the firstly synthesis of nataural and analogues bioactive compounds in batch and flow mode using supported catalysts