B(C6F5)3-Catalyzed redox-neutral β-alkylation of tertiary amines using p-quinone methides via borrowing hydrogen
1Hubei Collaborative Innovation Centre for Advanced Organic Chemical Materials, College of Chemistry and Chemical Engineering, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan, 430062, P. R. China. machao@hubu.edu.cn yangguichun@hubu.edu.cn.
Abstract:
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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