Rh[III]-Catalyzed Direct C-H Amination Using N-Chloroamines at Room Temperature

被引:236
作者
Grohmann, Christoph [1 ]
Wang, Honggen [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
基金
欧洲研究理事会;
关键词
CATALYZED DIRECT AMINATION; BOND FORMATION; OXIDATIVE OLEFINATION; ACID-DERIVATIVES; DIRECT ARYLATION; EFFICIENT; FUNCTIONALIZATION; ACTIVATION; REACTIVITY; AMIDATION;
D O I
10.1021/ol203353a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Rh(III)-catalyzed direct C-H amination of N-pivaloyloxy benzamides with N-chloroamines proceeding at room temperature was achieved. The versatile directing group allows for selective mono- and diamination and can be readily converted to give valuable benzamide or aminoaniline derivatives. Mechanistic studies have been carried out to elucidate the reaction pathway.
引用
收藏
页码:656 / 659
页数:4
相关论文
共 81 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Thermodynamic characterization of allosteric glycogen phosphorylase inhibitors [J].
Anderka, Oliver ;
Loenze, Petra ;
Klabunde, Thomas ;
Dreyer, Matthias K. ;
Defossa, Elisabeth ;
Wendt, K. Ulrich ;
Schmoll, Dieter .
BIOCHEMISTRY, 2008, 47 (16) :4683-4691
[4]   Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles [J].
Armstrong, Alan ;
Collins, James C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2282-2285
[5]   Umpolung Amination: Nickel-Catalyzed Coupling Reactions of N,N-Dialkyl-N-chloroamines with Diorganozinc Reagents [J].
Barker, Timothy J. ;
Jarvo, Elizabeth R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) :15598-+
[6]   CHEMISTRY OF HYDROXAMIC ACIDS AND N-HYDROXYIMIDES [J].
BAUER, L ;
EXNER, O .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (06) :376-384
[7]   RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].
Besset, Tatiana ;
Kuhl, Nadine ;
Patureau, Frederic W. ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171
[8]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[9]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[10]   Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].
Cho, Seung Hwan ;
Yoon, Jungho ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005