Alexandria Digital Research Library

Recent Advances in Palladium-Catalyzed Kumada-Corriu Couplings

Author:
Haley, Stephen Douglas
Degree Grantor:
University of California, Santa Barbara. Chemistry
Degree Supervisor:
Bruce H. Lipshutz
Place of Publication:
[Santa Barbara, Calif.]
Publisher:
University of California, Santa Barbara
Creation Date:
2012
Issued Date:
2012
Topics:
Chemistry, Organic
Genres:
Online resources and Dissertations, Academic
Dissertation:
M.S.--University of California, Santa Barbara, 2012
Description:

Since the early 1970's transition metal-catalyzed cross-coupling reactions have been a major part of the landscape of synthetic chemistry. Among these reactions palladium-catalyzed reactions have attracted special attention due to their mild conditions and the high degree of functional group tolerance displayed by palladium salts. Despite the remarkable progress made in advancing the field of palladium-catalyzed cross-coupling reactions in the last forty years there exist substantial limitation to the use of palladium catalysts in the presence of substrates bearing beta-hydrogen atoms due to the facile beta-hydride elimination reaction associated with palladium salts. In the interest of expanding the utility of these palladium salt catalysts we investigated the possibility of utilizing a sterically hindered palladium-phosphine complex to facilitate rapid cross-coupling reactions of beta-hydride bearing Grignard reagents in the Kumada-Corriu reaction. We discovered that when a catalytic system composed of catalytic (dtbpf)PdCl2 and stoichiometric amounts of the diamine ligand TMEDA was employed we were able to selectively cross-couple alkenyl halides with beta-hydride bearing Grignard reagents in excellent yields with minimal side-product formation.

Physical Description:
1 online resource (63 pages)
Format:
Text
Collection(s):
UCSB electronic theses and dissertations
ARK:
ark:/48907/f3m61h58
ISBN:
9781267649836
Catalog System Number:
990038915380203776
Rights:
Inc.icon only.dark In Copyright
Copyright Holder:
Stephen Haley
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