Journal
CHEMCATCHEM
Volume 6, Issue 12, Pages 3547-3552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201402767
Keywords
carbenes; organocatalysis; polynorbornene; supported catalysts; umpolung
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Funding
- Spanish MINECO (DGI) [CTQ2010-18901/BQU, CTQ2013-48406-P]
- MEC (FPU)
- Junta de Castilla y Leon [VA302U13]
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A bromoalkyl functionalized vinylic addition polynorbornene has been used as an inert new scaffold to support imidazolium salts by straightforward nucleophilic substitution using different imidazoles ImR (R=Me, mesityl, 2,6-iPr(2)C(6)H(3)). These polymers, VA-PNB-(CH2)(4)ImRBr, are precursors of N-heterocyclic carbenes which are useful as heterogeneous organocatalysts. The polymeric carbenes have been tested in two model reactions: The synthesis of saturated esters from alpha,beta-unsaturated aldehydes and the conjugate umpolung reaction of alpha,beta-unsaturated aldehydes for the synthesis of gamma-butyrolactones. The supported catalyst (R=mesityl) is fully recyclable and can be recovered as an imidazolium salt and stored for further use.
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