EPFL doctorate Award 2012 - Oleg Vechorkin

“For his remarkable thesis work on the discovery and development of nickel-catalyzed cross coupling and C-H functionalization reactions using nonactivated alkyl halides as electrophiles”

Abstract: Complexity and size of organic molecules in chemical and pharmaceutical research grows constantly, making their synthesis more and more challenging. Recent developments in the transition metal catalyzed cross coupling reactions make this method an efficient and fast way of synthesizing organic molecules. The coupling of non-activated alkyl halides however is still very problematic. Efficient solutions for this important class of compounds were found during our research work. We prepared a well-defined and easily synthesized nickel pincer complex [(MeN2N)Ni-Cl]. This complex is an efficient catalyst for Kumada and Sonogashira coupling of non-activated alkyl halides and direct C-H alkylation. The activity and selectivity of the catalyst was checked on a wide range of substrates. The products of the reactions were separated in good to excellent yields. The reactions are chemo-selective and tolerate many important functional groups. Moreover, in the presence of different halide atoms in the molecule, several coupling reactions can be done consecutively, allowing access to compounds bearing several functional groups. One of the biggest advantages is the versatility of this catalyst, allowing the use of the same catalyst for a wide range of coupling reactions. Utilization of this catalyst and developed methodologies in the laboratorial and industrial processes can improve and facilitate the synthesis of important organic compounds and pharmaceutical products.