Abstract:
Oxidative addition and reductive elimination are two fundamental steps common to many different catalytic reactions. Insertion into C-X bonds is particularly prevalent as one of the first steps in a catalytic cycle.
We have been exploring the synthetic potential associated with reversible oxidative addition into carbon-halogen bond and recently developed a metal catalyzed carboiodination reaction (1-2). This lecture will describe the scope and limitations of the reaction including recent work that has expanded the scope and led to the development of a metal catalyzed hydrohalogenation reaction (3).
C-H functionalization remains one of the most active areas of research. We will present our recent work in this field highlighting C-H bond activation as a key step in spirocyclization reactions (4-5).
References
(1) Newman, S.G.; Lautens, M. Journal of the American Chemical Society 2011, 133, 1778-1780.
(2) Petrone, D.A.; Le, C.; Newman, S.G.; Lautens, M. New Trends in Cross Coupling: Theory and Applications, RSC, Colacot, T. Ed. 2014.
(3) Petrone, D.A.; Franzoni, I.; Ye, J.; Rodriguez, J.; Poblador-Bahamonde, A.; Lautens, M. Journal of the American Chemical Society, 2017, 139, 3546
(4) Ye, J. ; Shi, Z.; Sperger, T.; Yasukawa, Y.; Kingston, C.; Schoenebeck, F.; Lautens, M. Nature Chemistry, 2017, 9, 361-368.
(5) (4) Yoon, H.; Rolz, M; Lossouarn, A.; Landau, F.; Lautens, M. Angewandte Chemie International Edition, 2017, 56, 10920-10923