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A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection
Alan C Spivey1, David J Turner, Michael L Turner
1Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK. a.c.spivey@sheffield.ac.uk
Organic Letters
|May 25, 2002
Abstract:
[reaction: see text] A new iterative synthesis of regioregular oligothiophenes has been developed in which "double-coupling" after each iteration minimizes deletion sequences. The method exploits the susceptibility of alpha-silyl- but not alpha-germyl-substituted thiophene derivatives toward nucleophilic ipso-protodemetalation and features an unusual "base-free" Suzuki-type cross-coupling protocol. The strategy has been designed for the solid-phase synthesis of high purity oligothiophenes using a germanium-based linker.