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Palladium- and Nickel-Catalyzed Amination of Aryl Fluorosulfonates

 spectroscopy, SYNTHESIS  Comments Off on Palladium- and Nickel-Catalyzed Amination of Aryl Fluorosulfonates
May 132016
 
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Examples of the palladium- and nickel-catalyzed amination of aryl fluorosulfonates with aromatic and alkyl amines are described. Aniline is coupled to a diverse series of aryl fluorosulfonates catalyzed by the combination of CpPd(cinammyl) and Xantphos, and the relative reactivity of aryl fluorosulfonates to undergo Pd-catalyzed amination was compared with other common aryl electrophiles. In addition, we report the direct amination of a phenol by in situ formation of an aryl fluorosulfonate by reaction with sulfuryl fluoride and base followed by subsequent amination to form a new C–N bond. Finally, we report examples of the nickel-catalyzed amination of aryl fluorosulfonates catalyzed by the combination of Ni(COD)2 and DPPF in the presence of MeCN. The high reactivity of the aryl fluorosulfonate electrophile with generic palladium and nickel catalyst systems, combined with its simple preparation from sulfuryl fluoride will enable commercial amination reactions of abundant phenolic raw materials.

SEE…….http://pubs.acs.org/doi/full/10.1021/acscatal.6b00865

Palladium- and Nickel-Catalyzed Amination of Aryl Fluorosulfonates

The Dow Chemical Company, Core R&D, Midland, Michigan 48674, United States
ACS Catal., 2016, 6, pp 3515–3519
DOI: 10.1021/acscatal.6b00865
Publication Date (Web): April 27, 2016
Copyright © 2016 American Chemical Society

ACS Editors’ Choice – This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

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////Palladium, Nickel-Catalyzed , Amination , Aryl Fluorosulfonates

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