Topics in Organometallic Chemistry | Year: 2012
A synthesis of an aryl boronic acid and the subsequent Suzuki coupling to an aryl indole has been developed and successfully scaled up to pilot plant scale. The Suzuki coupling was optimized by design of experiments and run with a catalyst loading of 0.1 mol%. The article describes the strategic approach for the optimization of the reaction and the most critical issues, such as the cryogenic synthesis of the boronic acid, the catalyst optimization, and the palladium removal, are discussed in detail. Graphical Abstract: © 2012 Springer-Verlag Berlin Heidelberg.
Indolese A.F.,RohnerChem |
Girling K.,RohnerChem |
Chimica Oggi | Year: 2010
Low temperature reactions and transition metal catalysis (TMC) have emerged as powerful tools in organic synthesis in the past few years. Complex aromatic molecules can be easily synthesized by combining the cryogenic lithiation and TMC technologies. The differences and the synergies of these reaction types are discussed in the context of industrial relevant molecules. The specific advantages of the two technologies are demonstrated on examples of the synthesis of benzoic acid and biphenyl derivatives.