Degree Type
Dissertation
Date of Award
2003
Degree Name
Doctor of Philosophy
Department
Chemistry
First Advisor
Richard C. Larock
Abstract
Palladium-catalyzed intramolecular C-H activation of o-halobiaryls has been used to carry out important chemical transformations. For instance, in the presence of catalytic amounts of Pd(0), o-halobiaryls are readily cyclocarbonylated under an atmosphere of CO to produce fluorenones in high yields with good regioselectivity. This methodology has been successfully applied to the preparation of polycyclic fluorenones and fluorenones containing fused isoquinoline, indole, pyrrole, thiophene, benzothiophene, and benzofuran rings.;A novel 1,4-Pd migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this unique C-H activation-migration process have been trapped by way of a Heck reaction and Suzuki-Miyaura cross-coupling with arylboronic acids. Similarly, organopalladium intermediates generated by 1,4-Pd migration have been trapped by intramolecular arylation to produce fused polycycles. This unique migration-arylation methodology have been used to prepare complex polycyclic compounds containing fused benzofuran, quinoline, oxepine, indole, phenanthrene, and naphthalene rings.
DOI
https://doi.org/10.31274/rtd-180813-10921
Publisher
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu
Copyright Owner
Marino Andres Campo Molina
Copyright Date
2003
Language
en
Proquest ID
AAI3085891
File Format
application/pdf
File Size
352 pages
Recommended Citation
Campo Molina, Marino Andres, "Advances in C-H activation by palladium: migration and cyclocarbonylation " (2003). Retrospective Theses and Dissertations. 566.
https://lib.dr.iastate.edu/rtd/566
