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. 2017 Jan 11;139(1):115-118.
doi: 10.1021/jacs.6b12712. Epub 2016 Dec 23.

Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals

Zhe Zhou  1 , Zhiwei Ma  1 , Nicole Erin Behnke  1 , Hongyin Gao  1 , László Kürti  1
Affiliations

Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals

Zhe Zhou et al. J Am Chem Soc. .

Abstract

Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl- as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or directing groups. This one-pot transformation allows unprecedented functional group tolerance and it is well-suited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper(I) salt is required.

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Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Representative methods for the precious metal-free electrophilic amination of arylmetals.
Figure 2
Figure 2
Proposed mechanistic pathways.
See this image and copyright information in PMC

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