Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for polymerisation

Iain A. Liversedge; Simon J. Higgins; Mark Giles; Martin Heeney; Iain McCulloch

doi:10.1016/j.tetlet.2006.05.063

Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for polymerisation

Iain A. Liversedge, Simon J. Higgins, Mark Giles, Martin Heeney, Iain McCulloch

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

We have applied palladium complexes of bulky, electron-rich phosphane ligands as catalysts for the Suzuki synthesis of highly head-to-tail regioregular polyalkylthiophenes from 2-(5-bromo-4-n-alkyl-thiophen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. The monomer can be prepared in high yield by Ir-catalysed borylation of 2-bromo-3-hexylthiophene, without the need for organolithium reagents or strong bases.

Original language	English (US)
Pages (from-to)	5143-5146
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.063
State	Published - Jul 17 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.05.063

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title = "Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for polymerisation",

abstract = "We have applied palladium complexes of bulky, electron-rich phosphane ligands as catalysts for the Suzuki synthesis of highly head-to-tail regioregular polyalkylthiophenes from 2-(5-bromo-4-n-alkyl-thiophen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. The monomer can be prepared in high yield by Ir-catalysed borylation of 2-bromo-3-hexylthiophene, without the need for organolithium reagents or strong bases.",

author = "Liversedge, {Iain A.} and Higgins, {Simon J.} and Mark Giles and Martin Heeney and Iain McCulloch",

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Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for polymerisation. / Liversedge, Iain A.; Higgins, Simon J.; Giles, Mark et al.
In: Tetrahedron Letters, Vol. 47, No. 29, 17.07.2006, p. 5143-5146.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for polymerisation

AU - Liversedge, Iain A.

AU - Higgins, Simon J.

AU - Giles, Mark

AU - Heeney, Martin

AU - McCulloch, Iain

PY - 2006/7/17

Y1 - 2006/7/17

N2 - We have applied palladium complexes of bulky, electron-rich phosphane ligands as catalysts for the Suzuki synthesis of highly head-to-tail regioregular polyalkylthiophenes from 2-(5-bromo-4-n-alkyl-thiophen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. The monomer can be prepared in high yield by Ir-catalysed borylation of 2-bromo-3-hexylthiophene, without the need for organolithium reagents or strong bases.

AB - We have applied palladium complexes of bulky, electron-rich phosphane ligands as catalysts for the Suzuki synthesis of highly head-to-tail regioregular polyalkylthiophenes from 2-(5-bromo-4-n-alkyl-thiophen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. The monomer can be prepared in high yield by Ir-catalysed borylation of 2-bromo-3-hexylthiophene, without the need for organolithium reagents or strong bases.

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DO - 10.1016/j.tetlet.2006.05.063

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SN - 0040-4039

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SP - 5143

EP - 5146

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for polymerisation

Abstract

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