Work

Friedel–Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis

Year: 2012

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo300162c

Authors: Chunhui Dai, Francesco Meschini, Jagan M. R. Narayanam, Corey R. J. Stephenson

Institution: Boston University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green