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Reliable Suzuki Chemistry For Functionalised Polythiophene Synthesis

Published online by Cambridge University Press:  01 February 2011

Simon Higgins
Affiliation:
shiggins@liv.ac.uk, University of Liverpool, Chemistry, Crown Street, Liverpool, L69 7ZD, United Kingdom
Iain Liversedge
Affiliation:
iain_liversedge@hotmail.co.uk, University of Liverpool, Chemistry, Crown Street, Liverpool, L69 7ZD, United Kingdom
Samer Badriya
Affiliation:
sbadriya@liverpool.ac.uk, University of Liverpool, Chemistry, Crown Street, Liverpool, L69 7ZD, United Kingdom
Martin Heeney
Affiliation:
Martin.Heeney@merckchem.co.uk, Merck Chemicals, Chilworth Technical Centre, Southampton, SO16 7QD, United Kingdom
Mark Giles
Affiliation:
Mark.Giles@merckchem.co.uk, Merck Chemicals, Chilworth Technical Centre, Southampton, SO16 7QD, United Kingdom
Iain McCulloch
Affiliation:
Iain.McCulloch@merckchem.co.uk, Merck Chemicals, Chilworth Technical Centre, Southampton, SO16 7QD, United Kingdom
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Abstract

Until recently, the synthesis of polythiophenes using Suzuki chemistry has proven difficult because of the ready protodeborylation of thiophene boronates. However, we now report that the new generation of bulky, electron-rich Pd(0)-phosphane catalysts are effective and reliable for the preparation of regioregular polyalkylthiophenes using Suzuki coupling. Moreover, the monomers can be prepared in high yield by Ir-catalysed borylation, without the need for strong organolithium bases, making this potentially a highly functional group-tolerant approach to polyalkylthiophene derivatives. Perfluoroalkylthiophenes also undergo this reaction.

Type
Research Article
Copyright
Copyright © Materials Research Society 2007

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