Friedel-Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis

被引：181

作者：

Dai, Chunhui ^{[1
]}

Meschini, Francesco ^{[1
]}

Narayanam, Jagan M. R. ^{[1
]}

Stephenson, Corey R. J. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 09期

基金：

瑞士国家科学基金会;

关键词：

VISIBLE-LIGHT PHOTOCATALYSIS; N-ACYLIMINIUM IONS; C-H BOND; PHOTOREDOX CATALYSIS; ELECTROCHEMICAL REDUCTION; CHEMISTRY; CONVERSION; MECHANISM; PEROXYDISULFATE; COMPLEXES;

D O I：

10.1021/jo300162c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Friedel Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S2O82-) 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.

引用

页码：4425 / 4431

页数：7

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