Rhodium-catalysed tandem dehydrogenative coupling-Michael addition: direct synthesis of phthalides from benzoic acids and alkenes

被引：23

作者：

Renzetti, Andrea ^{[1
,2
,3
]}

Nakazawa, Hiroshi ^{[2
]}

Li, Chao-Jun ^{[3
]}

机构：

[1] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

[2] Osaka City Univ, Grad Sch Sci, Dept Chem, Osaka 5588585, Japan

[3] McGill Univ, Dept Chem, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada

来源：

RSC ADVANCES | 2016年 / 6卷 / 47期

基金：

日本学术振兴会; 加拿大自然科学与工程研究理事会;

关键词：

C-H ACTIVATION; INTERNAL ALKYNES; CARBOXYLIC-ACIDS; BOND FORMATION; EFFICIENT; RH; CYCLOMETALATION; DERIVATIVES; ANNULATION; CHEMISTRY;

D O I：

10.1039/c6ra07671h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[(COD)RhCl](2) catalyses the coupling of benzoic acids and alkenes in the presence of Cu(OAc)(2)center dot H2O and dicyclopentadiene to afford phthalides in 15-93% yield. A 3-substituted or 3,7-disubstituted product is obtained selectively depending on alkene type. The reaction is highly atom-economical and uses readily available starting materials.

引用

页码：40626 / 40630

页数：5

共 3 条

[1] New Synthesis of Furans: the Rhodium-Catalysed Carbonylative Addition of Arylboronic Acids to Propargylic Alcohols/Cyclisation Sequence
Dheur, Julien
Sauthier, Mathieu
Castanet, Yves
Mortreux, Andre
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 557 - 561
[2] A Novel Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of 3-Substituted Phthalides from Aldehydes and Aromatic Acids
Shi, Xianying
Li, Chao-Jun
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2933 - 2938
[3] A Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of N- Substituted Phthalimides from Isocyanates and Benzoic Acids
Shi, Xian-Ying
Renzetti, Andrea
Kundu, Soumen
Li, Chao-Jun
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) : 723 - 728

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