134640-47-4Relevant academic research and scientific papers
Metal-free oxidative coupling reactions via ω-iodonium intermediates: The efficient synthesis of bithiophenes using hypervalent iodine reagents
Morimoto, Koji,Nakae, Tomofumi,Yamaoka, Nobutaka,Dohi, Toshifumi,Kita, Yasuyuki
experimental part, p. 6326 - 6334 (2011/12/02)
The direct oxidative biaryl coupling reaction is an attractive tool for environmentally benign green chemistry. A novel direct method for the synthesis of bithiophene using a hypervalent iodine reagent has been developed. The reaction mechanism has also been investigated, casting light on the reaction intermediate and revealing the reactivity with iodonium salts.
Polymer-Supported Synthesis of Regioregular Head-to-Tail-Coupled Oligo(3-arylthiophene)s Utilizing a Traceless Silyl Linker
Briehn, Christoph A.,Kirschbaum, Thomas,Baeuerle, Peter
, p. 352 - 359 (2007/10/03)
The solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-arylthiophene)s has been achieved in high yield and purity by using a traceless silyl ether linkage. In the first step, the solution-phase synthesis of this class of conjugated oligomers was investigated. Benzyl alcohol was chosen to serve as a mimic for the anchoring group of the hydroxymethyl-substituted polystyrene matrix. The development of a novel regioselective iodination process for silyl-protected thiophenes faciliates the successful application of the solution-phase protocol to the solid phase. Satisfactory loading was obtained by reaction of chlorosilyl-functionalized 3-arylthiophene with hydroxymethyl polystyrene in the presence of imidazole. The suitability of the following iterative halogenation and Suzuki cross-coupling sequence is illustrated by the preparation of a quater(3-arylthiophene), the first regioregular head-to-tail-coupled oligothiophene that is synthesized on solid support. Removal of the conjugated oligomers from the solid support could be effectively achieved by treatment with tetrabutylammonium fluoride.
Synthesis of 3,4'-Diaryl- and 4,4'-Diaryl-2,2'-bithienyls from 2,5-Dichlorothiophene
Sone, Tyo,Umetsu, Yasuhiro,Sato, Kazuaki
, p. 864 - 868 (2007/10/02)
3,4'-Diaryl- and 4,4'-diaryl-2,2'-bithienyls, new classes of mixed thiophene-arene oligomers, were synthesized from 2,5-dichlorothiophene via 4-aryl-2-chlorothiophene in three and two steps, respectively.Namely, a Friedel-Crafts type self-condensation of 4-aryl-2-chlorothiophene, followed by catalytic dechlorination, yielded unsymmetrical bithienyls.Homocoupling of 4-aryl-2-chlorothiophene using a nickel-phosphine catalyst gave symmetrical bithienyls.
