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

被引:355
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
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
收藏
页码:8605 / 8608
页数:4
相关论文
共 66 条
[41]   Diaryliodonium Salts: A Journey from Obscurity to Fame [J].
Merritt, Eleanor A. ;
Olofsson, Berit .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9052-9070
[42]   Iodinated biaryls synthesized by the direct dehydrodimerization of iodoarenes using phenyliodine(III) bis(trifluoroacetate) (PIFA) [J].
Mirk, D ;
Willner, A ;
Fröhlich, R ;
Waldvogel, SR .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (06) :675-681
[43]  
Monnier F., 2009, Angew. Chem, V121, P7088, DOI DOI 10.1002/ANGE.200804497
[44]   Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions [J].
Monnier, Florian ;
Taillefer, Marc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :6954-6971
[45]   Organohypervalent iodine: Development, applications, and future directions [J].
Moriarty, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :2893-2903
[46]  
Neumann J.J., 2009, Angew. Chem., V121, P7024
[47]   Palladium-Catalyzed Amidation of Unactivated C(sp3)-H Bonds: from Anilines to Indolines [J].
Neumann, Julia J. ;
Rakshit, Souvik ;
Droege, Thomas ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) :6892-6895
[48]   Iodobenzene-catalyzed α-acetoxylation of ketones.: In situ generation of hypervalent (diacyloxyiodo)benzenes using m-chloroperbenzoic acid [J].
Ochiai, M ;
Takeuchi, Y ;
Katayama, T ;
Sueda, T ;
Miyamoto, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12244-12245
[49]   Stoichiometric and catalytic oxidations with hypervalent organo-λ3-iodanes [J].
Ochiai, Masahito .
CHEMICAL RECORD, 2007, 7 (01) :12-23
[50]   PALLADIUM-CATALYZED FORMATION OF CARBON-NITROGEN BONDS - REACTION INTERMEDIATES AND CATALYST IMPROVEMENTS IN THE HETERO CROSS-COUPLING OF ARYL HALIDES AND TIN AMIDES [J].
PAUL, F ;
PATT, J ;
HARTWIG, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5969-5970