Synfacts 2024; 20(09): 0931
DOI: 10.1055/s-0043-1775024
Metals in Synthesis

Synthesis of Oximes by Nickel-Catalyzed Coupling of Nitrates with Organohalides

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Phillip Pommerening
Padmanaban S, Chun J, Lee Y, Cho K.-B, *, Choi J, *, Lee Y. * Jeonbuk National University, Jeonju, Chonnam National University, Gwangju and Seoul National University, Republic of Korea
Nitrate Upcycling Mediated by Organonickel Catalysis.

Angew. Chem. Int. Ed. 2024; e202408457
DOI: 10.1002/anie.202408457.
 

Significance

A nickel-catalyzed protocol for the selective coupling of nitrate salts with organohalides to form oximes is disclosed. This method represents a new strategy for upcycling the environmental pollutant nitrate into synthetically valuable chemicals.


#

Comment

X-ray structures of catalyst intermediates and DFT calculations support the shown mechanism. While the conversion of aromatic alkyl halides proceeded smoothly, purely aliphatic halides showed no reaction or gave only traces of product.


#
#

Publication History

Article published online:
16 August 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany