title: Copper-catalyzed Huisgen and oxidative Huisgen coupling reactions controlled by polysiloxane-supported amines (AFPs) for the divergent synthesis of triazoles and bistriazoles.
abstract: 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.
authors.affiliation: Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, PR China.
authors.forename: Zhan-Jiang
authors.initials: ZJ
authors.lastname: Zheng
authors.forename: Fei
authors.initials: F
authors.lastname: Ye
authors.forename: Long-Sheng
authors.initials: LS
authors.lastname: Zheng
authors.forename: Ke-Fang
authors.initials: KF
authors.lastname: Yang
authors.forename: Guo-Qiao
authors.initials: GQ
authors.lastname: Lai
authors.forename: Li-Wen
authors.initials: LW
authors.lastname: Xu
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D058451:Oxidative Coupling; D012833:Siloxanes / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D012833:Siloxanes; D014230:Triazoles; D003300:Copper