Premium
Copper‐Catalyzed Huisgen and Oxidative Huisgen Coupling Reactions Controlled by Polysiloxane‐Supported Amines (AFPs) for the Divergent Synthesis of Triazoles and Bistriazoles
Author(s) -
Zheng ZhanJiang,
Ye Fei,
Zheng LongSheng,
Yang KeFang,
Lai GuoQiao,
Xu LiWen
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202472
Subject(s) - chemistry , amine gas treating , cycloaddition , oxidative coupling of methane , click chemistry , catalysis , copper , combinatorial chemistry , polymer chemistry , coupling reaction , organic chemistry
An interesting example of a divergent catalysis with a copper(I) and amine‐functional macromolecular polysiloxanes system was successfully presented in click chemistry. In this manuscript, we demonstrate the remarkable ability of the secondary amine‐functional polysiloxane to induce oxidative coupling in the copper‐mediated Huisgen reactions of azides and alkynes, thereby achieving good yields and selectivities. The click reactions mediated by a polysiloxane‐supported secondary amine allow the preparation of novel heterocyclic compounds, that is, bistriazoles. Comparably, it is also surprising that the use of a diamine‐functional polysiloxane as ligand led to a classic Huisgen [3+2] cycloaddition in excellent yields. From the results of the present amine‐functional polysiloxanes‐controlled Huisgen reaction or oxidative Huisgen coupling reaction to divergent products and the proposed mechanism, we suggested that the mononuclear bistriazole–copper complex stabilized and dispersed by the secondary amine‐functional polysiloxane was beneficial to prevalent the way to oxidative coupling.