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. 2012 May 4;77(9):4425-31.
doi: 10.1021/jo300162c. Epub 2012 Apr 18.

Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis

Chunhui Dai  1 , Francesco Meschini, Jagan M R Narayanam, Corey R J Stephenson
Affiliations

Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis

Chunhui Dai et al. J Org Chem. .

Abstract

Friedel-Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S(2)O(8)(2-)) in the presence of the visible light catalyst, Ru(bpy)(3)Cl(2), at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron-rich arenes served as effective nucleophiles, forming new C-O or C-C bonds. In general, photocatalysis provided higher yields and better selectivities.

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Figures

Scheme 1
Scheme 1
α-C–H Functionalization of Amines and Amides via Visible Light-Mediated Photocatalysis
Scheme 2
Scheme 2
Formation of N,O-Aminals
Scheme 3
Scheme 3
A Plausible Reaction Mechanism
See this image and copyright information in PMC

References

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