4.7 Article

B(C6F5)3-Catalyzed redox-neutral -alkylation of tertiary amines using p-quinone methides via borrowing hydrogen

Journal

CHEMICAL COMMUNICATIONS
Volume 55, Issue 9, Pages 1217-1220

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc09215j

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Funding

  1. National Natural Science Foundation of China [21702053]
  2. Ministry of Education of Singapore [R-143-000-613-112]

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Herein, we present the first example of catalytic redox-neutral -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(sp(3))-H bond at the -position of acyclic tertiary amines through conjugate addition to para-quinone methides. Compared to previous work on direct -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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