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Issue 107, 2016, Issue in Progress
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p-Bromoaryl- and ω-bromoalkyl-VA-PNBs: suitable starting materials for the functionalization of vinylic addition polynorbornenes via palladium-catalyzed cross-coupling reactions

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Abstract

New vinylic addition polynorbornenes (VA-PNBs) with a variable amount of pendant 4-bromoaryl groups have been synthesized by homo- and copolymerization with norbornene of 2-(4-bromophenyl)-5-norbornene catalyzed by [Ni(C6F5)2(SbPh3)2]. These polymers can be transformed by Pd-catalyzed cross coupling reactions into VA-PNBs with pendant diaryl (Suzuki), alkenyl and ketoalkyl (Stille) and amino (Buchwald–Hartwig) groups. Although the cross-coupling reactions of alkylhalides are more difficult, (ω-bromobutyl)-VA-PNBs can also be functionalized by a Suzuki reaction with arylboronic acids. This results open up new ways of post-polymerization functionalization of VA-PNBs, quite attractive for their robust, thermally stable and transparent skeleton.

Graphical abstract: p-Bromoaryl- and ω-bromoalkyl-VA-PNBs: suitable starting materials for the functionalization of vinylic addition polynorbornenes via palladium-catalyzed cross-coupling reactions

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Publication details

The article was received on 16 Sep 2016, accepted on 30 Oct 2016 and first published on 31 Oct 2016


Article type: Paper
DOI: 10.1039/C6RA23123C
Citation: RSC Adv., 2016,6, 105878-105887
  • Open access: Creative Commons BY-NC license
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    p-Bromoaryl- and ω-bromoalkyl-VA-PNBs: suitable starting materials for the functionalization of vinylic addition polynorbornenes via palladium-catalyzed cross-coupling reactions

    S. Martínez-Arranz, E. Sánchez-Pérez, J. A. Molina de la Torre, I. Pérez-Ortega and A. C. Albéniz, RSC Adv., 2016, 6, 105878
    DOI: 10.1039/C6RA23123C

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