Document Server@UHasselt >
Research >
Research publications >

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
MAES, Wouter
LUTSEN, Laurence
CLEIJ, Thomas J.
Botek, Edith
Champagne, Benoit
Issue Date: 2010
Citation: 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
URI: http://hdl.handle.net/1942/11475
DOI: 10.1021/jo101405j
ISI #: 000283531100018
ISSN: 0022-3263
Category: A1
Type: Journal Contribution
Validation: ecoom, 2011
Appears in Collections: Research publications

Files in This Item:

There are no files associated with this item.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.