Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature

被引：356

作者：

Antonchick, Andrey P. ^{[1
]}

Samanta, Rajarshi ^{[1
]}

Kulikov, Katharina ^{[1
]}

Lategahn, Jonas ^{[1
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 37期

关键词：

amination; C-H functionalization; hypervalent compounds; iodine; organocatalysis; HYPERVALENT IODINE CHEMISTRY; CARBON-NITROGEN BONDS; NATURAL-PRODUCTS; ARYL HALIDES; PALLADIUM; COPPER; FUNCTIONALIZATION; SUBSTITUTION; GENERATION; CARBAZOLE;

D O I：

10.1002/anie.201102984

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The twinkling of an I: In a new atom-economical and environmentally friendly organocatalytic method for intramolecular C-H amination, the C-N bond forms at ambient temperature by abstraction of two atoms of hydrogen; only acetic acid and water are formed as by-products. The method has also been extended to the unprecedented metal-free cross-amination of nonactivated arenes. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8605 / 8608

页数：4

共 66 条

[11] Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant [J].

Dohi, T ;

Maruyama, A ;

Yoshimura, M ;

Morimoto, K ;

Tohma, H ;

Kita, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6193-6196

[12]

Dohi T., 2005, ANGEW CHEM, V117, P6349, DOI DOI 10.1002/ANGE.200501688

[13]

Dohi T., 2010, ANGEW CHEM, V122, P3406, DOI 10.1002/ange.200907281

[14] Oxidative cross-coupling of arenes induced by single-electron transfer leading to biaryls by use of organoiodine(III) oxidants [J].

Dohi, Toshifumi ;

Ito, Motoki ;

Morimoto, Koji ;

Wata, Minako ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) :1301-1304

[15] First hypervalent iodine(III)-catalyzed C-N bond forming reaction:: catalytic spirocyclization of amides to N-fused spirolactams [J].

Dohi, Toshifumi ;

Maruyama, Akinobu ;

Minamitsuji, Yutaka ;

Takenaga, Naoko ;

Kita, Yasuyuki .

CHEMICAL COMMUNICATIONS, 2007, (12) :1224-1226

[16] Discovery of Stabilized Bisiodonium Salts as Intermediates in the Carbon-Carbon Bond Formation of Alkynes [J].

Dohi, Toshifumi ;

Kato, Daishi ;

Hyodo, Ryo ;

Yamashita, Daisuke ;

Shiro, Motoo ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (16) :3784-3787

[17] Designer μ-oxo-bridged hypervalent iodine(III) organocatalysts for greener oxidations [J].

Dohi, Toshifumi ;

Takenaga, Naoko ;

Fukushima, Kei-ichiro ;

Uchiyama, Teruyoshi ;

Kato, Daishi ;

Shiro, Motoo ;

Fujioka, Hiromichi ;

Kita, Yasuyuki .

CHEMICAL COMMUNICATIONS, 2010, 46 (41) :7697-7699

[18] Fluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts [J].

Dohi, Toshifumi ;

Yamaoka, Nobutaka ;

Kita, Yasuyuki .

TETRAHEDRON, 2010, 66 (31) :5775-5785

[19] Unusual ipso Substitution of Diaryliodonium Bromides Initiated by a Single-Electron-Transfer Oxidizing Process [J].

Dohi, Toshifumi ;

Ito, Motoki ;

Yamaoka, Nobutaka ;

Morimoto, Koji ;

Fujioka, Hiromichi ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (19) :3334-3337

[20] Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent [J].

Dohi, Toshifumi ;

Ito, Motoki ;

Yamaoka, Nobutaka ;

Morimoto, Koji ;

Fujioka, Hiromichi ;

Kita, Yasuyuki .

TETRAHEDRON, 2009, 65 (52) :10797-10815

← 1 2 3 4 5 6 7 →