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Development and applications of palladium(0)-catalyzed-C(sp3)-H activation

Dailler, David. Development and applications of palladium(0)-catalyzed-C(sp3)-H activation. 2017, Doctoral Thesis, University of Basel, Faculty of Science.

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Official URL: http://edoc.unibas.ch/diss/DissB_12657

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Abstract

Over the last decade, the transition metal-catalyzed intramolecular activation of unactivated CH
bonds has emerged as a powerful method to transform otherwise inert entities allowing access
to molecular complexity in an atom- and step-economical fashion.
Research in our group is centered on the activation and functionalization of C(sp3)-H bonds that
lead to the development of new methodologies and applications including asymmetric catalysis,
mechanistic studies and total synthesis of complex molecules.
Recently, our group developed a straightforward access to hexahydroindoles scaffolds by
intramolecular C(sp3)-H alkenylation. As a follow-up, we first investigated the application of
this new methodology in combination with a directed C(sp3)-H arylation to achieve a collective
synthesis of aeruginosins.
In a second part, we extended this methodology to the development of a modular C(sp3)-H
alkenylation for the synthesis of a wide variety of g -lactams, which are prevalent scaffolds
found in numerous bioactive natural molecules.
Finally, we developed a highly efficient synthesis of b-lactams, which are valuable compounds
widely used in pharmaceutical chemistry, by palladium(0)-catalyzed-C(sp3)-H carbamoylation.
Keywords : C-H functionalization, C-H activation, organometallic catalysis, palladium, total
synthesis, aeruginosins, g-lactams, b-lactams
Advisors:Baudoin, Olivier and Gademann, Karl
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Dailler, David and Baudoin, Olivier and Gademann, Karl
Item Type:Thesis
Thesis Subtype:Doctoral Thesis
Thesis no:12657
Thesis status:Complete
Bibsysno:Link to catalogue
Number of Pages:1 Online-Ressource (297 Seiten)
Language:English
Identification Number:
Last Modified:19 Jun 2018 04:30
Deposited On:18 Jun 2018 10:05

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