A Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of N- Substituted Phthalimides from Isocyanates and Benzoic Acids

被引:65
作者
Shi, Xian-Ying [1 ,2 ,3 ]
Renzetti, Andrea [1 ]
Kundu, Soumen [1 ]
Li, Chao-Jun [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada
[2] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710062, Peoples R China
[3] Key Lab Macromol Sci Shaanxi Prov, Xian 710062, Peoples R China
基金
加拿大自然科学与工程研究理事会;
关键词
amidation; CH activation; cascade cyclization; isocyanates; phthalimides; rhodium; C-H BOND; ONE-STEP SYNTHESIS; CARBONYLATION REACTIONS; EFFICIENT SYNTHESIS; AROMATIC KETIMINES; CYCLIC IMIDES; IONIC LIQUID; ARYL; ACTIVATION; PALLADIUM;
D O I
10.1002/adsc.201300834
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A rhodium(III)-catalyzed amidation between benzoic acids and isocyanates via direct functionalization of an ortho C-H bond followed by intramolecular cyclization is described. This cascade cyclization affords N-substituted phthalimides in one step in 26-91% yields. The reaction is highly atom-economical, since no theoretical waste except for water is generated in the reaction.
引用
收藏
页码:723 / 728
页数:6
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