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Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

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.

SUBMITTER: Dai C

PROVIDER: S-EPMC3360956 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

Dai Chunhui C Meschini Francesco F Narayanam Jagan M R JM Stephenson Corey R J CR

The Journal of organic chemistry 20120418 9

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 ...[more]

PMID: 22458307

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