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Synfacts 2020; 16(06): 0687
DOI: 10.1055/s-0040-1706966
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Electrophilic Amination of Diorganozinc Reagents Using N-Hydroxylamine Benzoates

Contributor(s):
Paul Knochel
,
Simon Graßl
Berman AM, Johnson JS. * University of North Carolina at Chapel Hill, USA
Copper-Catalyzed Electrophilic Amination of Diorganozinc Reagents.

J. Am. Chem. Soc. 2004;
126: 5680-5681
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Further Information

Publication History

Publication Date:
15 May 2020 (online)

 
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Key words

electrophilic amination - organozinc reagents - copper catalysis

Significance

In 2004, Berman and Johnson developed the first electrophilic amination of N-hydroxylamine benzoates using diorganozinc reagents in the presence of [Cu(OTf)]2·C6H6. This umpolung-type reaction allowed access to a broad range of highly functionalized secondary and tertiary amines under mild conditions.


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Comment

The outstanding performance of N-hydroxylamine benzoates as electrophilic nitrogen sources has inspired various following publications, opening up new opportunities for amination reactions. Based on experimental studies, the authors excluded an oxidative addition/reductive elimination pathway and proposed a SN2-type pathway. For further insights into electrophilic aminations based on this pioneering work, see: Synthesis 2011, 24, 3954–3964.


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