Perspective on Ruthenium-Copper-Mediated Dehydrogenative C-N Bond Formation

被引:23
作者
Biafora, Agostino [1 ]
Patureau, Frederic W. [1 ]
机构
[1] Kaiserslautern Univ Technol, Dept Chem, Kaiserslautern, Germany
关键词
C-H activation; oxidative amination; dehydrogenative cross-coupling; axial chirality; lauternamines; H BONDS; REDUCTIVE ELIMINATION; CARBON-CARBON; CARBAZOLE; AMINATION; FUNCTIONALIZATION; DERIVATIVES; AMIDATION;
D O I
10.1055/s-0034-1378999
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In 2014, the direct dehydrogenative construction of ubiquitous C-N bonds remains a significant challenge, but recent communications in this field show that this is about to change. Here we highlight a novel ruthenium-catalyzed method for C-H activation and dehydrogenative C-N cross-coupling of unprotected diarylamines in an intermolecular fashion, with carbazoles. The resulting compounds, lauternamines, show unexpected and unprecedented H-bonded stabilized axial chirality. These promise new exciting developments in C-N dehydrogenative couplings.
引用
收藏
页码:2525 / 2530
页数:6
相关论文
共 38 条
[1]   SYNTHESIS OF CARBAZOLE ALKALOIDS [J].
BERGMAN, J ;
PELCMAN, B .
PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1967-1976
[2]   Conjugated Polymers Based on a S- and N-Containing Heteroarene: Synthesis, Characterization, and Semiconducting Properties [J].
Chen, Yagang ;
Tian, Hongkun ;
Yan, Donghang ;
Geng, Yanhou ;
Wang, Fosong .
MACROMOLECULES, 2011, 44 (13) :5178-5185
[3]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[4]   Insertion reactions of GaCp*, InCp* and In[C(SiMe3)3] into the Ru-Cl bonds of [(p-cymene)RuIICl2]2 and [Cp*RuIICl]4 [J].
Cokoja, M ;
Gemel, C ;
Steinke, T ;
Schröder, F ;
Fischer, RA .
DALTON TRANSACTIONS, 2005, (01) :44-54
[5]   Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds [J].
Dick, AR ;
Sanford, MS .
TETRAHEDRON, 2006, 62 (11) :2439-2463
[6]   Carbon-nitrogen-bond-forming reductive elimination of arylamines from palladium(II) phosphine complexes [J].
Driver, MS ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (35) :8232-8245
[7]  
Espino CG, 2001, ANGEW CHEM INT EDIT, V40, P598, DOI 10.1002/1521-3773(20010202)40:3<598::AID-ANIE598>3.0.CO
[8]  
2-9
[9]   Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation [J].
Espino, CG ;
Wehn, PM ;
Chow, J ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6935-6936
[10]   New efficient nickel-catalyzed cross-coupling reaction between two Csp3 centers [J].
Giovannini, R ;
Stüdemann, T ;
Devasagayaraj, A ;
Dussin, G ;
Knochel, P .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3544-3553