Iron-Catalyzed ortho C-H Arylation and Methylation of Pivalophenone N-H Imines

ChemSusChem
Wengang Xu, Naohiko Yoshikai

Abstract

Iron-catalyzed ortho C-H arylation and methylation reactions of pivalophenone N-H imines are reported. The pivaloyl N-H imine proved an excellent directing group for the arylation with diarylzinc reagents in the presence of an iron-diphosphine catalyst and 2,3-dichlorobutane at room temperature. A similar catalytic system also allowed methylation with Me3 Al at 70 °C. The pivaloyl imine of the product could be readily converted to a cyano group, thus allowing convenient preparation of ortho-functionalized benzonitriles.

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Citations

Oct 9, 2020·Angewandte Chemie·Shengjun NiLukasz T Pilarski
Mar 11, 2021·Chemical Society Reviews·Daniya AynetdinovaDarren J Dixon
Aug 8, 2019·The Journal of Organic Chemistry·Roshayed Ali Laskar, Naohiko Yoshikai

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