Recent Advances in Palladium-Catalyzed Kumada-Corriu Couplings
- 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
- Other Versions:
- http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqm&rft_dat=xri:pqdiss:1519479
- ARK:
- ark:/48907/f3m61h58
- ISBN:
- 9781267649836
- Catalog System Number:
- 990038915380203776
- Copyright:
- Stephen Haley, 2012
- Rights:
- In Copyright
- Copyright Holder:
- Stephen Haley
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