Palladium-Catalyzed Cross -Coupling Reactions of Organosilanolates: Methods Development and Application in the Total Synthesis of (+)-Papulacandin D
Regens, Christopher
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https://hdl.handle.net/2142/84337
Description
Title
Palladium-Catalyzed Cross -Coupling Reactions of Organosilanolates: Methods Development and Application in the Total Synthesis of (+)-Papulacandin D
Author(s)
Regens, Christopher
Issue Date
2009
Doctoral Committee Chair(s)
Denmark, Scott E.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
Finally, an E,Z-1,4-bissilylbutadiene reagent was prepared for the synthesis of unsymmetrical, highly conjugated systems. Two distinct silyl substituents were differentiated in the cross-coupling reaction through the initial use of base-promoted reaction conditions where only one silyl group was reactive with a range of aryl halides. The second silyl substituent then reacted under fluoride-promoted reaction conditions to provide the desired unsymmetrical products.
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