You are invited to attend a special seminar by:
Dr. Joseph S. M. Samec
Department of Chemistry,
University of Uppsala,
Sweden
Friday 10th April 2015
10:50–12:00
Room 1119 MHMK (main auditorium)
Functional Group Interconversion of Non-Derivatized Alcohols by Catalysis
Functional group interconversion (FGI) of the hydroxyl group in an alcohol is still a major challenge in organic
synthesis. Traditionally, FGI is performed in two separate reaction steps in which the hydroxyl group is
converted into a better leaving group, such as a mesyl- or tosyl group or a halide. In a second reaction step, a
nucleophile is charged by a strong base to promote the substitution.
Our group is working on developing catalytic procedures to substitute the hydroxyl group without prior
derivatization by uncharged nucleophiles by means of catalysis. We base our development of synthetic
procedures on mechanistic studies including; kinetics, isolation of reactive intermediates, labeling studies and
DFT calculations.
I will present recent results concerning our studies on Pd-catalyzed allylic amination reactions,1 Pd-catalyzed
transfer hydrogenolysis reactions with applications to lignin valorization,2 and Brönsted acid catalyzed
stereospecific substitution reactions of alcohols.3
References:
1.
2.
3.
(a) Sawadjoon, S.; Sjöberg, P. J. R.; Orthaber, A.; Matsson, O.; Samec, J. S. M. Chem.- A Eur. J., 2014, 20, 1520; (b)
Supaporn S.; Orthaber, A.; Sjöberg, P. J. R.; Eriksson, L.; Samec, J. S. M. Organometallics, 2014, 33, 249-253.
(a) Galkin, M. V.; Sawadjoon, S.; Rohde, V.; Dawange, M.; Samec, Jo. S. M. ChemCatChem, 2014, 6, 179-184; (b)
Sawadjoon, S.; Lundstedt, A.; Samec, J. S. M. ACS Catalysis, 2013, 3, 635-642. (b) Galkin, M. V.; Dahlstrand, C.,
Samec, J. S. M. ChemSusChem, 2015, DOI:10.1002/cssc.201500117 (c) Galkin, Maxim, Samec, Joseph ChemSusChem
2014, 7, 2154; (d) Dawange, Monali; Galkin, Maxim V.; Samec, Joseph S. M. ChemCatChem 2015, 7, 401.
Bunrit, Anon; Dahlstrand, Christian; Olsson, Sandra K.; Srifa, Pemikar; Huang, Genping; Orthaber, Andreas; Sjöberg,
Per; Biswas, Srijit; Himo Fahmi; Samec, Joseph S. M. J. Am. Chem. Soc., 2015, DOI: 10.1021/jacs.5b02013
---------------------------------------------------------------------------------------------------------------------------Joseph Samec received his Ph.D. in Organic Chemistry from University of Stockholm in 2005. After a
postdoctoral training with Robert H. Grubbs at CaltTech during 2006-2007, he was appointed an
Assistant Professorship at University of Uppsala in Sweden. He is currently a Secondary Lecturer at
Uppsala University. His research interest focuses on green chemistry in organic synthesis.
For more details please contact: Dr. Tirayut Vilaivan
Organic Synthesis Research Unit