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Beilstein J Org Chem. 2009 Apr 14;5:11. doi: 10.3762/bjoc.5.11.

Convenient methods for preparing pi-conjugated linkers as building blocks for modular chemistry.

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  • 1Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, nám Cs. legií 565, Pardubice, 532 10, Czech Republic.

Abstract

Simple, straightforward and optimized procedures for preparing extended pi-conjugated linkers are described. Either unsubstituted or 4-donor substituted pi-linkers bearing a styryl, biphenyl, phenylethenylphenyl, and phenylethynylphenyl pi-conjugated backbone are functionalized with boronic pinacol esters as well as with terminal acetylene moieties allowing their further use as building blocks in Suzuki-Miyaura or Sonogashira coupling reactions.

KEYWORDS:

Sonogashira reaction; Suzuki–Miyaura reaction; boronic acid; donor/acceptor; linker; property tuning; push-pull

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