O&B Section Seminar Professor O Boudoin
Lecture Theatre 3
Professor Olivier Boudoin from the University of Basel will be visiting the School of Chemistry.
The lecture is entitled "Direct vs. migratory Pd-catalyzed cross-coupling"
Our group's research is mainly focusing on the functionalization of non-activated C(sp3)-H bonds under catalysis by palladium(0) complexes. A first strategy, which we have been pursuing for the past 15 years relies on intramolecular C-H activation and allows for the creation of a variety of interesting ring systems from simple precursors. More recently, we have investigated a different strategy for the intermolecular functionalization of remote C(sp3)-H bonds via a Pd "chain-walk" mechanism.2 We showed that the site-selectivity of the cross-coupling on the alkyl chain can be controlled by the ligand, with bulky phosphines giving rise to the direct coupling
product whereas homemade conformationally flexible ligands favor the migratory coupling product. This lecture will present this concept in the context of two cross-couplings: the arylation of ester enolates3 and the Negishi coupling.4
1. O. Baudoin, Acc. Chem. Res. 2017, 50, 1114.
2. O. Baudoin, Chima 2016, 70, 768.
3. a) A. Renaudat, L. Jean-Gérard, R. Jazzar, C. E. Kefalidis, E. Clot, O. Baudoin, Angew. Chem. Int. Ed. 2010, 49,
7261; b) P. Larini, C. E. Kefalidis, R. Jazzar, A. Renaudat, E. Clot, O. Baudoin Chem. Eur. J. 2012, 18, 1932; c) S. Aspin,
A.-S. Goutierre, P. Larini, R. Jazzar, O. Baudoin, Angew. Chem. Int. Ed. 2012, 51, 10808 ; d) S. Aspin, L. López-Suárez,
P. Larini, A.-S. Goutierre, R. Jazzar, O. Baudoin, Org. Lett. 2013, 15, 5056; e) A. Martin, J.-P. Vors, O. Baudoin, ACS
Catal. 2016, 6, 3941.
4. a) A. Millet, P. Larini, E. Clot, O. Baudoin, Chem. Sci. 2013, 4, 2241 ; b) A. Millet, D. Dailler, P. Larini, O. Baudoin,
Angew. Chem. Int. Ed. 2014, 53, 2678; c) S. Dupuy, K.-F. Zhang, A.-S. Goutierre, O. Baudoin, Angew. Chem. Int. Ed.
2016, 55, 14793; d) T. Royal, Y. Baumgartner, O. Baudoin, Org. Lett. 2017, 19, 166; e) K.-F. Zhang, F. Christoffel, O.
Baudoin, Angew. Chem. Int. Ed. 2018, 57, 1982.