Synthesis of Oxindoles by Iron-Catalyzed Oxidative 1,2-Alkylarylation of Activated Alkenes with an Aryl C(sp2)H Bond and a C(sp3)H Bond Adjacent to a Heteroatom

被引：393

作者：

Wei, Wen-Ting ^{[1
]}

Zhou, Ming-Bo ^{[1
]}

Fan, Jian-Hong ^{[1
]}

Liu, Wei ^{[1
]}

Song, Ren-Jie ^{[1
]}

Liu, Yu ^{[1
]}

Hu, Ming ^{[1
,2
]}

Xie, Peng ^{[1
,2
]}

Li, Jin-Heng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 13期

关键词：

alkenes; difunctionalization; ethers; iron; oxindoles; C-H BONDS; ASYMMETRIC INTRAMOLECULAR ARYLATION; EFFICIENT SYNTHESIS; ALPHA-ARYLATION; CARBENE LIGAND; HECK REACTION; FUNCTIONALIZATION; CLEAVAGE; CARBON; OXIDE;

D O I：

10.1002/anie.201210029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Difunctionalization: Inexpensive and environmentally benign FeCl 3 catalyzes the oxidative 1,2-alkylarylation of activated alkenes with an aryl C(sp2)-H bond and a C(sp3)-H bond adjacent to a heteroatom. This reaction is a new strategy for the synthesis of oxindoles and makes use of DBU as ligand and TBHP as oxidant (see scheme, TBHP=tert-butyl hydrogenperoxide). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3638 / 3641

页数：4

共 89 条

[1] Air-Stable Secondary Phosphine Oxide as Preligand for Palladium-Catalyzed Intramolecular α-Arylations with Chloroarenes [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Hofmann, Nora .

ORGANIC LETTERS, 2009, 11 (19) :4274-4276

[2]

[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206

[3]

[Anonymous], 2011, ANGEW CHEM-GER EDIT

[4] Development of an N-heterocyclic carbene ligand based on concept of chiral mimetic [J].

Arao, T ;

Kondo, K ;

Aoyama, T .

TETRAHEDRON LETTERS, 2006, 47 (09) :1417-1420

[5] Synthesis of 2-oxindole derivatives via the intramolecular Heck reaction on solid support [J].

Arumugam, V ;

Routledge, A ;

Abell, C ;

Balasubramanian, S .

TETRAHEDRON LETTERS, 1997, 38 (36) :6473-6476

[6] CATALYTIC ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF PHYSOSTIGMINE - FORMATION OF QUATERNARY CARBON CENTERS WITH HIGH ENANTIOSELECTION BY INTRAMOLECULAR HECK REACTIONS OF (Z)-2-BUTENANILIDES [J].

ASHIMORI, A ;

MATSUURA, T ;

OVERMAN, LE ;

POON, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6949-6951

[7]

Bernardinelli G., 2007, ANGEW CHEM, V119, P8636, DOI DOI 10.1002/ANGE.200703408

[8] Transition-Metal-Free Synthesis of Oxindoles by Potassium tert-Butoxide-Promoted intramolecular α-Arylation [J].

Beyer, Astrid ;

Buendia, Julien ;

Bolm, Carsten .

ORGANIC LETTERS, 2012, 14 (15) :3948-3951

[9] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[10] Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction [J].

Bonnaterre, Florence ;

Bois-Choussy, Michele ;

Zhu, Jieping .

ORGANIC LETTERS, 2006, 8 (19) :4351-4354

← 1 2 3 4 5 6 7 8 9 →