FeCl3-Catalyzed Oxidative Allylation of sp2 and sp3 C-H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines

被引：85

作者：

Kumaraswamy, Gullapalli ^{[1
]}

Murthy, Akula Narayana ^{[1
,2
]}

Pitchaiah, Arigala ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 3, Hyderabad 500007, Andhra Pradesh, India

[2] Univ Hyderabad, Associate Inst, Hyderabad 500046, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 11期

关键词：

CATALYZED AEROBIC OXIDATION; EFFICIENT SYNTHESIS; SECONDARY-AMINES; SODIUM-CYANIDE; IMINES; DEHYDROGENATION; SYSTEM; ALKYNYLATION; ACTIVATION; CYANATION;

D O I：

10.1021/jo1005813

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative allylation to sp(2)- and sp(3)-carbon attached to the nitrogen atom was accomplished. The alpha-allylation of tertiary amines was catalyzed by easily available hydrated iron(III) chloride in combination with air or aqueous (BuOOH)-Bu-t. Remarkably, N-allyl- and N-propagyl-tethered tertiary amines were also allylated through this protocol.

引用

页码：3916 / 3919

页数：4

共 42 条

[1] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].

Basle, Olivier ;

Li, Chao-Jun .

CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126

[2] CuBr-Catalyzed Oxidative Difluoromethylation of Tertiary Amines with Difluoroenol Silyl Ethers [J].

Chu, Lingling ;

Zhang, Xingang ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2009, 11 (10) :2197-2200

[3] Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran [J].

Davies, HML ;

Hansen, T ;

Churchill, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3063-3070

[4]

Davies HML, 2002, ANGEW CHEM INT EDIT, V41, P2197, DOI 10.1002/1521-3773(20020617)41:12<2197::AID-ANIE2197>3.0.CO

[5]

2-N

[6]

DOYLE S, 2001, ANGEW CHEM INT EDIT, V40, P3551

[7] Dehydrogenation of aromatic amines to imines via ruthenium-catalyzed hydrogen transfer [J].

Éll, AH ;

Samec, JSM ;

Brasse, C ;

Bäckvall, JE .

CHEMICAL COMMUNICATIONS, 2002, (10) :1144-1145

[8] Highly active and selective gold catalysts for the aerobic oxidative condensation of benzylamines to imines and one-pot, two-step synthesis of secondary benzylamines [J].

Grirrane, Abdessamad ;

Corma, Avelino ;

Garcia, Hermenegildo .

JOURNAL OF CATALYSIS, 2009, 264 (02) :138-144

[9] Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines [J].

Han, Wei ;

Ofial, Armin R. .

CHEMICAL COMMUNICATIONS, 2009, (40) :6023-6025

[10] Iron catalyzed oxidative cyanation of tertiary amines [J].

Han, Wei ;

Ofial, Armin R. .

CHEMICAL COMMUNICATIONS, 2009, (33) :5024-5026

← 1 2 3 4 5 →