Journal
CHEMCATCHEM
Volume 11, Issue 1, Pages 424-429Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201801361
Keywords
helical polymer; click reaction; screw-sense induction; N-heterocyclic carbine; reusable catalyst
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Funding
- JSPS KAKENHI [JP15H05811]
- Japan Science and Technology Corporation (CREST)
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Poly(quinoxaline-2,3-diyl)s (PQXs) bearing 1,2,3-triazole pendants were synthesized by living copolymerization of achiral 1,2-diisocyanobenzenes or by post-polymerization functionalization of PQXs bearing alkyne pendants through copper-catalyzed azide-alkyne cycloaddition. Thus prepared PQXs bearing 1,2,3-triazole pendants were treated with MeI, Ag2O, and AuCl successively, giving polymer-supported gold complexes bearing 1,2,3-triazolylidenes as abnormal N-heterocyclic carbene (aNHC) ligands. The polymer-based aNHC ligand served as a catalyst for the reaction of styrene with a propargylic ester to form a cyclopropane derivative. The catalyst could be reused at least eight times without loss of activity.
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