B(C₆F₅)₃-Catalyzed redox-neutral β-alkylation of tertiary amines using p-quinone methides via borrowing hydrogen
2019
Li, Rui | Chen, Yong | Jiang, Kun | Wang, Feiyi | Lu, Cuifen | Nie, Junqi | Chen, Zuxing | Yang, Guichun | Chen, Ying-Chun | Zhao, Yu | Ma, Chao
Herein, we present the first example of catalytic redox-neutral β-functionalization of tertiary amines through a borrowing hydrogen process. This B(C₆F₅)₃-catalyzed procedure utilizes commercially or readily available catalysts and substrates and promotes a direct functionalization of the C(sp³)–H bond at the β-position of acyclic tertiary amines through conjugate addition to para-quinone methides. Compared to previous work on direct β-functionalization of tertiary amines under oxidative conditions, besides being metal-free, the significant advantage of this method is that neither stoichiometric oxidants nor reductants are needed which may otherwise generate unnecessary waste.
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