Literature DB >> 22458307

Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

Chunhui Dai1, Francesco Meschini, Jagan M R Narayanam, Corey R J Stephenson.   

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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Year:  2012        PMID: 22458307      PMCID: PMC3360956          DOI: 10.1021/jo300162c

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


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