Copper-Catalyzed Intramolecular C H Oxidation/Acylation of Formyl-N-arylformamides Leading to Indoline-2,3-diones

被引：200

作者：

Tang, Bo-Xiao ^{[1
]}

Song, Ren-Jie ^{[1
]}

Wu, Cui-Yan ^{[1
]}

Liu, Yu ^{[1
]}

Zhou, Ming-Bo ^{[1
]}

Wei, Wen-Ting ^{[1
]}

Deng, Guo-Bo ^{[1
]}

Yin, Du-Lin ^{[1
]}

Li, Jin-Heng ^{[1
]}

机构：

[1] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 26期

关键词：

COUPLING REACTION; BOND ACTIVATION; DIRECT ACCESS; ARYL IODIDES; PALLADIUM; ARYLATION; ALDEHYDES; ISATINS; ACID; CHEMISTRY;

D O I：

10.1021/ja103426d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new, efficient Cu-catalyzed intramolecular C-H oxidation/acylation method has been developed for the synthesis of substituted indoline-2,3-diones (isatins). In the presence of CuCl, and O-2, a variety of formyl-N-arylformamides underwent the tandem reaction to afford the corresponding indoline-2,3-diones in moderate to good yields. It is noteworthy that the reaction serves as the first example of transition-metal-catalyzed transformation for the preparation of indoline-2,3-diones.

引用

页码：8900 / +

页数：4

共 57 条

[1] Pd-Catalyzed Intramolecular Acylation of Aryl Bromides via C-H Functionalization: A Highly Efficient Synthesis of Benzocyclobutenones
Alvarez-Bercedo, Paula
Flores-Gaspar, Areli
Correa, Arkaitz
Martin, Ruben
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) : 466 - +
[2] Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4:: Synthesis of benzocyclic ketones
Barluenga, Jose
Trincado, Monica
Rubio, Eduardo
Gonzalez, Jose M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) : 3140 - 3143
[3] BENINCORI T, 1990, GAZZ CHIM ITAL, V120, P635
[4] Bonnefoy J., 1921, Rend, V172, P220
[5] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
Chen, Xiao
Hao, Xue-Shi
Goodhue, Charles E.
Yu, Jin-Quan
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
[6] Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives
Chen, Xiao
Dobereiner, Graham
Hao, Xue-Shi
Giri, Ramesh
Maugel, Nathan
Yu, Jin-Quan
[J]. TETRAHEDRON, 2009, 65 (16) : 3085 - 3089
[7] The chemistry of isatins: a review from 1975 to 1999
da Silva, JFM
Garden, SJ
Pinto, AC
[J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (03) : 273 - 324
[8] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
Daugulis, Olafs
Do, Hien-Quang
Shabashov, Dmitry
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) : 1074 - 1086
[9] Evaluation of three novel cholecystokinin-B/gastrin receptor antagonists: A study of their effects on rat stomach enterochromaffin-like cell activity
Ding, XQ
Lindstrom, E
Hakanson, R
[J]. PHARMACOLOGY & TOXICOLOGY, 1997, 81 (05): : 232 - 237
[10] Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds
Do, Hien-Quang
Daugulis, Olafs
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) : 1128 - +

← 1 2 3 4 5 6 →