Yahui Wang, PhD student under the supervision of Prof. Antonio M. Echavarren, has defended his PhD Thesis entitled “Gold Carbenes from Cycloheptatrienes: Generation and Fate” (assigned to the Organic and Analytical Chemistry Department of the Universitat Rovira i Virgili) publicly on July 25th at the ICIQ auditorium.
The members of his evaluation committee were: Prof. Miquel A. Pericàs (ICIQ), Dr. Rubén Vicente (Universidad de Oviedo) and Prof. Pedro J. Pérez (Universidad de Huelva).
Metal carbenes are one of the fundamental reactive intermediates in organic synthesis and have been widely used in the construction of complex molecules. Many transition metals are known to catalyze the decomposition of diazo derivatives as a powerful method for the generation of metal carbenes. Considering the interest of our research group on developing new gold-catalyzed transformations, we found a new method to generate gold(I) carbenes through the retro-Buchner reaction of the norcaradiene tautomer based on the known equilibrium of cycloheptatrienes and norcaradienes. Gold(I) carbenes generated by this method are highly reactive species and react with many kinds of nucleophiles to give various products, which are not easily prepared by other methods. Interestingly, this constituted a safer alternative to the use of rather explosive diazo compounds. This thesis presents the detailed studies of this new gold(I) carbene generation method, including: cyclopropanations, reaction with furans, formal (4+1) cycloaddition with cyclobutenes and methylenecyclopropanes (MCPs), formal sp2 C–H insertions.