Catalytic C-H Amination with Unactivated Amines through Copper(II) Amides

被引：150

作者：

Wiese, Stefan ^{[2
]}

Badiei, Yosra M. ^{[2
]}

Gephart, Raymond T. ^{[2
]}

Mossin, Susanne ^{[3
]}

Varonka, Matthew S. ^{[2
]}

Melzer, Marie M. ^{[2
]}

Meyer, Karsten ^{[3
]}

Cundari, Thomas R. ^{[1
]}

Warren, Timothy H. ^{[2
]}

机构：

[1] Univ N Texas, CASCaM, Dept Chem, Denton, TX 78203 USA

[2] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

[3] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91058 Erlangen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 47期

基金：

美国国家科学基金会;

关键词：

amide; amination; C-H functionalization; copper; BOND FORMATION; AMIDATION; COMPLEXES; FUNCTIONALIZATION; AZIRIDINATION; DERIVATIVES; CHEMISTRY; OXIDATION; INSIGHTS; ALKENES;

D O I：

10.1002/anie.201003676

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

En route to catalysis: Two equivalents of the three-coordinate copper(II) amide [(Cl2NN)Cu]-NHAd participate in stoichiometric C - H amination by a H-atom abstraction/radical capture sequence. This active species may be generated through a copper(II) tert-butoxide intermediate to allow for the unprecedented catalytic amination of sp3-C - H bonds with unactivated alkylamines. This method greatly expands the range of amines for catalytic C - H amination since most protocols require N-based electron-withdrawing groups. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8850 / 8855

页数：6

共 54 条

[1]

[Anonymous], 2008, ANGEW CHEM

[2] Theoretical Insights into Enantioselective Catalysis: The Mechanism of the Kharasch-Sosnovsky Reaction [J].

Antonio Mayoral, Jose ;

Rodriguez-Rodriguez, Sergio ;

Salvatella, Luis .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) :9274-9285

[3] Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study [J].

Au, SM ;

Huang, JS ;

Yu, WY ;

Fung, WH ;

Che, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9120-9132

[4]

Badiei Y.M., 2008, ANGEW CHEMIE, V120, P10109

[5] Copper-Nitrene Complexes in Catalytic C-H Amination [J].

Badiei, Yosra M. ;

Dinescu, Adriana ;

Dai, Xiliang ;

Palomino, Robert M. ;

Heinemann, Frank W. ;

Cundari, Thomas R. ;

Warren, Timothy H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9961-9964

[6] Catalytic C-H amination: recent progress and future directions [J].

Collet, Florence ;

Dodd, Robert H. ;

Dauban, Philippe .

CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074

[7] Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].

Constable, David J. C. ;

Dunn, Peter J. ;

Hayler, John D. ;

Humphrey, Guy R. ;

Leazer, Johnnie L., Jr. ;

Linderman, Russell J. ;

Lorenz, Kurt ;

Manley, Julie ;

Pearlman, Bruce A. ;

Wells, Andrew ;

Zaks, Aleksey ;

Zhang, Tony Y. .

GREEN CHEMISTRY, 2007, 9 (05) :411-420

[8]

Davies H.M. L., 2005, Angew. Chem, V117, P3584

[9] Recent advances in catalytic intramolecular C-H aminations [J].

Davies, HML ;

Long, MS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3518-3520

[10] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].

Davies, Huw M. L. ;

Manning, James R. .

NATURE, 2008, 451 (7177) :417-424

← 1 2 3 4 5 6 →