Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/11475
Title: A Three-Step Synthetic Approach to Asymmetrically Functionalized 4H-Cyclopenta[2,1-b:3,4-b ']dithiophenes
Authors: VAN MIERLOO, Sarah 
ADRIAENSENS, Peter J. 
MAES, Wouter 
LUTSEN, Laurence 
CLEIJ, Thomas J. 
Botek, Edith
Champagne, Benoit
VANDERZANDE, Dirk J. 
Issue Date: 2010
Publisher: AMER CHEMICAL SOC
Source: JOURNAL OF ORGANIC CHEMISTRY, 75 (21). p. 7202-7209
Abstract: A convenient and efficient three-step route toward both symmetrically and asymmetrically functionalized 4H-cyclopenta[2,1-b:3,4-b']dithiophenes has been developed. Using this method a broad collection of functionalized bridged bithiophenes can smoothly be accessed. Starting from 3-bromo2,2'-bithiophene, prepared by Kumada coupling of 2-thienylmagnesium bromide with 2,3-dibromothiophene under Pd(dppf)Cl-2 catalysis, lithiation and subsequent reaction with dialkyl ketones afforded (a)symmetrically dialkylated tertiary alcohol derivatives. By means of final Friedel Crafts dehydration cyclization in sulfuric acid medium, these derivatives were converted to 4,4-dialkyl-4H-cyclopenta[2,1-b:3,4-b']dithiophenes. Upon replacement of the alkyl ketone reagent by ethyl levulinate, an ester-functionalized 4H-cyclopenta[2,1-b:3,4-b']dithiophene was prepared, representing an attractive precursor for variously functionalized cyclopentadithiophene compounds.
Notes: [Van Mierloo, Sarah; Adriaensens, Peter J.; Maes, Wouter; Cleij, Thomas J.; Vanderzande, Dirk J.] Hasselt Univ, Inst Mat Res IMO, B-3590 Diepenbeek, Belgium. [Maes, Wouter] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium. [Lutsen, Laurence; Vanderzande, Dirk J.] IMEC, Div IMOMEC, B-3590 Diepenbeek, Belgium. [Botek, Edith; Champagne, Benoit] Fac Univ Notre Dame Paix, Chim Theor Lab, B-5000 Namur, Belgium. dirk.vanderzande@uhasselt.be
Document URI: http://hdl.handle.net/1942/11475
ISSN: 0022-3263
e-ISSN: 1520-6904
DOI: 10.1021/jo101405j
ISI #: 000283531100018
Category: A1
Type: Journal Contribution
Validations: ecoom 2011
Appears in Collections:Research publications

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