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Spivey AC, Turner DJ, Turner ML, et al. A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection. Org Lett. 2002;4(11):1899-902doi: 10.1021/ol025879x.
Spivey, A. C., Turner, D. J., Turner, M. L., & Yeates, S. (2002). A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection. Organic letters, 4(11), 1899-902. https://doi.org/10.1021/ol025879x
Spivey, Alan C, et al. "A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection." Organic letters vol. 4,11 (2002): 1899-902. doi: https://doi.org/10.1021/ol025879x
Spivey AC, Turner DJ, Turner ML, Yeates S. A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection. Org Lett. 2002 May 30;4(11):1899-902. doi: 10.1021/ol025879x. PMID: 12027642.
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Org Lett. 2002 May 30;4(11):1899-902. doi: 10.1021/ol025879x.

A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection.

Organic letters

Alan C Spivey, David J Turner, Michael L Turner, Stephen Yeates

Affiliations

  1. Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK. [email protected]

PMID: 12027642 DOI: 10.1021/ol025879x

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.

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