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 bonds and developed a palladium catalyzed carboiodination reaction.1 This lecture will describe the scope and limitations of the reaction including recent work that has expanded the synthetic utility by using other metals and chiral ligands. 2-3 We have also been exploring the value of combining catalysts and substrates in a multicomponent multicatalyst strategy (MC)2R.4,5 Recent advances will be presented.
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. Le, C.M.; Hou, X.; Sperger, T.; Schoenebeck, F.; Lautens, M.” An Exclusively trans-Selective Chlorocarbamoylation of Alkynes Enabled by a Palladium/Phosphaadamantane Catalyst” Angewandte Chemie International Edition 2015, 54, 15879-15900.
4. Panteleev, J.; Zhang, L.; Lautens, M. “Domino Rhodium-Catalyzed Alkyne Arylation/Palladium Catalyzed N Arylation: A Mechanistic Approach” Angewandte Chemie International Edition 2011, 48, 9089-9092.
5. Yamamoto, K.; Bruun, T.; Kim, J.Y.; Zhang, L.; Lautens, M. “A New Multicomponent Multicatalyst Reaction (MC)2R: Chemoselective Cycloaddition and Latent Catalyst Activation for the Synthesis of Fully Substituted 1,2,3-Triazoles” Organic Letters, 2016, 18, 2644-2647.