Organobismuth Reagents: Synthesis, Properties and Applications in Copper and Palladium-Catalyzed Reactions
Dr. Alex Gagnon(Universite du Quebec a Montreal)

ABSTRACT:  Organobismuth compounds are organometallic species that contain a C–Bi bond and that are easily prepared from inexpensive and low-toxic inorganic bismuth salts. Organobismuth compounds show unique reactivities which are modulated by the oxidation state of the bismuth center (+3, +5), the net charge of the compound (+2, +1, 0, –1), the number of coordinated groups (3 to 6), the ability of bismuth to form hypercoordinating interactions, the dual behavior of bismuth compounds as Lewis bases and soft Lewis acids, its borderline character between a metal and a non-metal and the high functional group tolerance of organobismuth compounds. Organobismuth species have been abundantly used in a wide diversity of metal-catalyzed reactions, enabling the facile construction of C–C, C–N, C–O and C–S bonds. This presentation will show our efforts in the field of organobismuth chemistry which led to the development of a portfolio of copper and palladium-catalyzed arylation and cyclopropylation reactions using organobismuth compounds.

BIO:  Professor Gagnon developed his passion for chemistry while attending an organic chemistry class given by Professor Roger Gauthier at College de Bois-de-Boulogne. After completion of his DEC degree, he pursued his education in chemistry at Université de Montréal as a Canada awardee, where he conducted some research in organometallic chemistry under the guidance of Professor Davit Zargarian. In 1995, he did a summer work term as an NSERC awardee in the laboratories of Professor André B. Charette.  Following the obtention of his B.Sc. diploma, he joined the group of Professor André B. Charette as an NSERC doctoral student, working on the double nucleophilic addition on nitriles and on the development of an unprecedented approach to the formation of geminal-dizinc carbenoid species and zincio-cyclopropanes.  In 2001, he joined the group of Professor Samuel J. Danishefsky at Columbia University as an NSERC post-doctoral student. There, he worked on the synthesis of Xestocyclamine A.  In 2003, Alex returned to Canada to work at Boehringer-Ingelheim Canada Ltd. as a research scientist where he was involved in the development of drugs for the treatment of viral infections (HIV, HCV).  After spending 4 months at Boehringer-Ingelheim in Austria, he did a brief return in the group of Professor Charette in 2009 as an independent researcher. In 2010, he moved to Cambridge, USA, where he joined the team of scientists at Constellation Pharmaceuticals, working in the emerging field of epigenetics.  In 2011, he accepted a faculty position in his home town, in the chemistry department of Université du Québec à Montréal (UQÀM).  Professor Gagnon has more than 25 publications and 8 patents. He is a member of Pharmaqam and of the center of green chemistry and catalysis.  He is also President of the Lucien-Piché Foundation and co-director of Pharmaqam.

Dr. Gagnon is the guest of Dr. Pat Forgione.