Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/silver-nitrate-catalyzed-n-arylation-of-amines-and-o-arylations-of-LN5Om4B04M
References (55)
-
Rachel Tundel, K. Anderson, S. Buchwald (2006)
Expedited palladium-catalyzed amination of aryl nonaflates through the use of microwave-irradiation and soluble organic amine bases.The Journal of organic chemistry, 71 1
-
M. Taillefer, Armelle Ouali, Brice-Loïc Renard, J. Spindler (2006)
Mild copper-catalyzed vinylation reactions of azoles and phenols with vinyl bromides.Chemistry, 12 20
-
L. Rout, P. Saha, Suribabu Jammi, T. Punniyamurthy (2008)
Cadmium(II)‐Catalyzed CN Cross‐Coupling of Amines with Aryl IodidesAdvanced Synthesis & Catalysis, 350
-
Longbin Liu, M. Frohn, N. Xi, C. Dominguez, R. Hungate, P. Reider (2005)
A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides.The Journal of organic chemistry, 70 24
-
Jingjun Yin, S. Buchwald (2002)
Pd-catalyzed intermolecular amidation of aryl halides: the discovery that xantphos can be trans-chelating in a palladium complex.Journal of the American Chemical Society, 124 21
-
K. Omura (1998)
Silver Ion-Mediated Coupling of 4-Bromo-2,6-di-tert-butylcycohexa-2,5-dienone with PhenolsJournal of Organic Chemistry, 63
-
E. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola (2007)
C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.Chemical reviews, 107 11
-
J. Corbet, G. Mignani (2006)
Selected patented cross-coupling reaction technologies.Chemical reviews, 106 7
-
A. Tlili, Florian Monnier, M. Taillefer (2012)
Selective one-pot synthesis of symmetrical and unsymmetrical di- and triarylamines with a ligandless copper catalytic system.Chemical communications
-
Florian Monnier, M. Taillefer (2009)
Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions.Angewandte Chemie, 48 38
-
E. Strieter, D. Blackmond, S. Buchwald (2005)
The role of chelating diamine ligands in the goldberg reaction: a kinetic study on the copper-catalyzed amidation of aryl iodides.Journal of the American Chemical Society, 127 12
-
J. Hartwig (2006)
Discovery and understanding of transition-metal-catalyzed aromatic substitution reactionsSynlett, 2006
-
Diliang Guo, He Huang, Jinyi Xu, Hualiang Jiang, Hong Liu (2008)
Efficient iron-catalyzed N-arylation of aryl halides with amines.Organic letters, 10 20
-
Kunbing Ouyang, Z. Xi (2013)
Roles of Bases in Transition-Metal Catalyzed Organic ReactionsActa Chimica Sinica, 71
-
Shiyu Chen, He Huang, Xuejun Liu, Jingkang Shen, Hualiang Jiang, Hong Liu (2008)
Microwave-assisted efficient copper-promoted N-arylation of amines with arylboronic acids.Journal of combinatorial chemistry, 10 3
-
M. Kantam, G. Venkanna, C. Sridhar, B. Sreedhar, B. Choudary (2006)
An efficient base-free N-arylation of imidazoles and amines with arylboronic acids using copper-exchanged fluorapatite.The Journal of organic chemistry, 71 25
-
Gavin Jones, Peng Liu, K. Houk, S. Buchwald (2010)
Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions.Journal of the American Chemical Society, 132 17
-
Arkaitz and, Carsten Prof. (2007)
Iron-Catalyzed N-Arylation of Nitrogen Nucleophiles†Angewandte Chemie, 119
-
J. Antilla, Jeremy Baskin, Timothy Barder, S. Buchwald (2004)
Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles.The Journal of organic chemistry, 69 17
-
Huifeng Wang, Yaming Li, Fangfang Sun, Yangyu Feng, Kun Jin, Xiunai Wang (2008)
1,2,3,4-Tetrahydro-8-hydroxyquinoline-promoted copper-catalyzed coupling of nitrogen nucleophiles and aryl bromides.The Journal of organic chemistry, 73 21
-
M. Taillefer, N. Xia, Armelle Ouali (2007)
Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles.Angewandte Chemie, 46 6
-
Artis Klapars, Xiaohua Huang, S. Buchwald (2002)
A general and efficient copper catalyst for the amidation of aryl halides.Journal of the American Chemical Society, 124 25
-
Yu Xia, Ouyang Zheng, R. Cooks (2008)
Peptide fragmentation assisted by surfaces treated with a low-temperature plasma in nanoESI.Angewandte Chemie, 47 45
-
B. Lipshutz, Bryan Frieman, T. Butler, V. Kogan (2006)
Heterogeneous Catalysis with Nickel‐on‐Graphite (Ni/Cg): Reduction of Aryl Tosylates and MesylatesAngewandte Chemie, 45
-
F. Monnier, Marc Taillefer (2008)
Katalytische C‐C‐, C‐N‐ und C‐O‐Ullmann‐KupplungenAngewandte Chemie, 121
-
H. Cristau, P. Cellier, J. Spindler, M. Taillefer (2004)
Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides.Chemistry, 10 22
-
H. Cristau, P. Cellier, J. Spindler, M. Taillefer (2004)
Mild Conditions for Copper‐Catalysed N‐Arylation of PyrazolesEuropean Journal of Organic Chemistry, 2004
-
10.1002/anie.200703299
Angew. Chem. Int. Ed., 46
-
Takashi Ikawa, Timothy Barder, M. Biscoe, S. Buchwald (2007)
Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation.Journal of the American Chemical Society, 129 43
-
J. Antilla, Artis Klapars, S. Buchwald (2002)
The copper-catalyzed N-arylation of indoles.Journal of the American Chemical Society, 124 39
-
S. Ley, Thomas William (2003)
Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond FormationAngewandte Chemie, 42
-
Wei Han, P. Mayer, Armin Ofial (2011)
Palladium‐katalysierte dehydrierende Kreuzkupplungen von Benzazolen mit AzolenAngewandte Chemie, 123
-
Rui Zhu, L. Xing, Xinyan Wang, Chuanjie Cheng, Deyong Su, Yuefei Hu (2008)
Highly Practical “Ligand‐Free‐Like” Copper‐Catalyzed N‐Arylation of Azoles in Lower Nitrile SolventsAdvanced Synthesis & Catalysis, 350
-
A. Correa, C. Bolm (2007)
Ligand-Free Copper-Catalyzed N-Arylation of Nitrogen NucleophilesAdvanced Synthesis & Catalysis, 349
-
Artis Klapars, J. Antilla, Xiaohua Huang, S. Buchwald (2001)
A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles.Journal of the American Chemical Society, 123 31
-
A. Tlili, Florian Monnier, M. Taillefer (2010)
Selective one-pot access to symmetrical or unsymmetrical diaryl ethers by copper-catalyzed double arylation of a simple oxygen source.Chemistry, 16 41
-
Jintang Zhang, Zuhui Zhang, Y. Wang, Xiaoqi Zheng, Zhiyong Wang (2008)
Nano‐CuO‐Catalyzed Ullmann Coupling of Phenols with Aryl Halides under Ligand‐Free ConditionsEuropean Journal of Organic Chemistry, 2008
-
F. Kwong, Artis Klapars, S. Buchwald (2002)
Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere.Organic letters, 4 4
-
Q. Shen, J. Hartwig (2007)
Lewis acid acceleration of C-N bond-forming reductive elimination from heteroarylpalladium complexes and catalytic amidation of heteroaryl bromides.Journal of the American Chemical Society, 129 25
-
F. Ullmann, J. Bielecki (1901)
Ueber Synthesen in der BiphenylreiheEuropean Journal of Inorganic Chemistry, 34
-
P. Saha, Md. Ali, Pokhraj Ghosh, T. Punniyamurthy (2010)
Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: synthesis of benzimidazoles and benzoxazoles.Organic & biomolecular chemistry, 8 24
-
Yu Yuan, Isabelle Thomé, S. Kim, D. Chen, A. Beyer, Julien Bonnamour, E. Zuidema, Sukbok Chang, C. Bolm (2010)
Dimethyl Sulfoxide/Potassium Hydroxide: A Superbase for the Transition Metal‐Free Preparation of Cross‐Coupling ProductsAdvanced Synthesis & Catalysis, 352
-
Lipshutz (2006)
10.1002/ange.200502887Angew. Chem., 118
-
Jesse Tye, Z. Weng, Adam Johns, C. Incarvito, J. Hartwig (2008)
Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides.Journal of the American Chemical Society, 130 30
-
W. Han, P. Mayer, A. Ofial (2011)
Palladium-catalyzed dehydrogenative cross-couplings of benzazoles with azoles.Angewandte Chemie, 50 9
-
G. Evano, N. Blanchard, M. Toumi (2008)
Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.Chemical reviews, 108 8
-
Xia (2008)
10.1002/ange.200803477Angew. Chem., 120
-
L. Rout, Suribabu Jammi, T. Punniyamurthy (2007)
Novel CuO nanoparticle catalyzed C-N cross coupling of amines with iodobenzene.Organic letters, 9 17
-
Taillefer (2007)
10.1002/ange.200603173Angew. Chem., 119
-
E. Strieter, Brijesh Bhayana, S. Buchwald (2008)
Mechanistic studies on the copper-catalyzed N-arylation of amides.Journal of the American Chemical Society, 131 1
-
I. Beletskaya, A. Cheprakov (2004)
Copper in cross-coupling reactions: The post-Ullmann chemistryCoordination Chemistry Reviews, 248
-
S. Murthy, B. Madhav, V. Reddy, Y. Nageswar (2010)
A New, Efficient and Recyclable Lanthanum(III) Oxide- Catalyzed CN Cross-CouplingAdvanced Synthesis & Catalysis, 352
-
Xiaohua Huang, K. Anderson, D. Zim, Lei Jiang, Artis Klapars, S. Buchwald (2003)
Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.Journal of the American Chemical Society, 125 22
-
S. Ley, Thomas William (2003)
Moderne Synthesemethoden: Kupfer-vermittelte C(Aryl)-O-, C(Aryl)-N- und C(Aryl)-S-VerknüpfungenAngewandte Chemie, 115
-
Per‐Fredrik Larsson, C. Bolm, P. Norrby (2010)
Kinetic investigation of a ligand-accelerated sub-mol% copper-catalyzed C-N cross-coupling reaction.Chemistry, 16 46
- Publisher
- Wiley
- Copyright
- Copyright © 2013 Wiley Subscription Services, Inc., A Wiley Company
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201300074
- Publisher site
- See Article on Publisher Site
Abstract
An efficient and general protocol for intermolecular CN and CO cross‐coupling of amines, alcohols, and phenols with halides has been developed by using AgNO3 as the catalyst and N,N‐dimethylethylenediamine (N,N‐DMEDA) as a ligand with KOtBu as a base in a nitrogen atmosphere. A number of primary, secondary, and heterocyclic amines were coupled with various aryl iodides to give N‐arylated motifs in good to excellent yield. Along with this, several substituted phenols as well as alcohols were coupled with various halides under the same reactions condition to give O‐arylated compounds.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Jul 1, 2013
Keywords: ; ; ; ;