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Helical Poly(quinoxaline‐2,3‐diyl)s Bearing 1,2,3‐Triazole Pendants: Synthesis by CuAAC and Use as Reusable Abnormal NHC Ligands in Gold Catalysis
Author(s) -
Zhang Pinglu,
Yamamoto Takeshi,
Suginome Michinori
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801361
Subject(s) - quinoxaline , cycloaddition , alkyne , chemistry , carbene , catalysis , polymer chemistry , triazole , ligand (biochemistry) , styrene , copolymer , combinatorial chemistry , click chemistry , azide , polymer , organic chemistry , biochemistry , receptor
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, Ag 2 O, 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.