Development and applications of palladium(0)-catalyzed-C(sp3)-H activation
Date Issued
2017
Author(s)
DOI
10.5451/unibas-006806222
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
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
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