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Part I. Large scale procedure for the α-arylation of esters catalyzed by the pd(i) dimer [p(tbu)3]pd(μ-br)]2. Part II. Palladium-catalyzed γ-arylation of α,β-unsaturated esters

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Title: Part I. Large scale procedure for the α-arylation of esters catalyzed by the pd(i) dimer [p(tbu)3]pd(μ-br)]2. Part II. Palladium-catalyzed γ-arylation of α,β-unsaturated esters
Author(s): Huang, David S.
Advisor(s): Hartwig, John F.
Department / Program: Chemistry
Discipline: Chemistry
Degree Granting Institution: University of Illinois at Urbana-Champaign
Degree: M.S.
Genre: Thesis
Subject(s): cross-coupling enolates homogeneous catalysis palladium
Abstract: We report the development of a procedure for the α-arylation of esters on 42 mmol scale which did not require use of a glovebox. The coupling of 3-bromoanisole and methyl isobutyrate catalyzed by 0.075 % [(P(tBu)3Pd(μ-Br)]2 occurred in 72% yield. The reaction was performed with commercially available reagents at a lab bench utilizing Schlenk technique. We report the γ-arylation of α,β-unsaturated esters in high yield with broad scope by coupling aryl, heteroaryl and vinyl halides with the corresponding silicon dienolates. These reactions occur in high yield with a variety of esters and with aromatic and vinylic electrophiles bearing potentially reactive functional groups. The coupling also proceeds in moderate to good yield for the coupling with silyl ketene acetals containing substitution at the α,β,γ- or δ-position. Moreover, these reactions occur without typical fluoride activators.
Issue Date: 2010-08-20
URI: http://hdl.handle.net/2142/16816
Rights Information: Copyright 2010 David S. Huang
Date Available in IDEALS: 2010-08-20
Date Deposited: 2010-08
 

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