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Issue 9, 2019
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B(C6F5)3-Catalyzed redox-neutral β-alkylation of tertiary amines using p-quinone methides via borrowing hydrogen

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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.

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

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Supplementary files

Article information


Submitted
20 Nov 2018
Accepted
21 Dec 2018
First published
21 Dec 2018

Chem. Commun., 2019,55, 1217-1220
Article type
Communication

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

R. Li, Y. Chen, K. Jiang, F. Wang, C. Lu, J. Nie, Z. Chen, G. Yang, Y. Chen, Y. Zhao and C. Ma, Chem. Commun., 2019, 55, 1217
DOI: 10.1039/C8CC09215J

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