Triazoles from N-alkynylheterocycles and their coordination to iridium

作者: Glenn A. Burley , Youcef Boutadla , David L. Davies , Kuldip Singh

DOI: 10.1021/OM201157G

关键词: BenzimidazoleOrganic chemistryChemistryDenticityClick chemistryIndazolePolymer chemistrySalt (chemistry)Iridium

摘要: N-alkynylheterocycles (benzimidazole and indazole) are converted to triazoles by click chemistry, the resulting react with [IrCl2Cp*]2. The benzimidazole-triazole coordinates in a monodentate fashion through benzimidazole, whereas indazole-triazole is bidentate coordination of both heterocycles. Reaction methyliodide gives benzimidazolium salt that deprotonates on afford rare example NHC–triazole.

参考文章(52)
Todd K. Hyster, Tomislav Rovis, Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H Activation Journal of the American Chemical Society. ,vol. 132, pp. 10565- 10569 ,(2010) , 10.1021/JA103776U
Damijana Urankar, Balazs Pinter, Andrej Pevec, Frank De Proft, Iztok Turel, Janez Košmrlj, Click-triazole N2 coordination to transition-metal ions is assisted by a pendant pyridine substituent. Inorganic Chemistry. ,vol. 49, pp. 4820- 4829 ,(2010) , 10.1021/IC902354E
Paulson Mathew, Antonia Neels, Martin Albrecht, 1,2,3-Triazolylidenes as Versatile Abnormal Carbene Ligands for Late Transition Metals Journal of the American Chemical Society. ,vol. 130, pp. 13534- 13535 ,(2008) , 10.1021/JA805781S
Stefan Warsink, Ruben M. Drost, Martin Lutz, Anthony L. Spek, Cornelis J. Elsevier, Modular Synthesis of Bidentate Triazolyl-Functionalized N-Heterocyclic Carbenes and Their Palladium Complexes Organometallics. ,vol. 29, pp. 3109- 3116 ,(2010) , 10.1021/OM100435X
Harriet Struthers, Thomas L. Mindt, Roger Schibli, Metal chelating systems synthesized using the copper(I) catalyzed azide-alkyne cycloaddition. Dalton Transactions. ,vol. 39, pp. 675- 696 ,(2010) , 10.1039/B912608B
David L. Davies, Steven M. A. Donald, Omar Al-Duaij, John Fawcett, Craig Little, Stuart A. Macgregor, N−H versus C−H Activation of a Pyrrole Imine at {Cp*Ir}:  A Computational and Experimental Study Organometallics. ,vol. 25, pp. 5976- 5978 ,(2006) , 10.1021/OM060863M
H. Nandivada, X. Jiang, J. Lahann, Click Chemistry: Versatility and Control in the Hands of Materials Scientists Advanced Materials. ,vol. 19, pp. 2197- 2208 ,(2007) , 10.1002/ADMA.200602739
Christoph Ulbricht, Beatrice Beyer, Christian Friebe, Andreas Winter, Ulrich S. Schubert, Recent Developments in the Application of Phosphorescent Iridium(III) Complex Systems Advanced Materials. ,vol. 21, pp. 4418- 4441 ,(2009) , 10.1002/ADMA.200803537
Shengtong Sun, Peiyi Wu, Mechanistic insights into Cu(I)-catalyzed azide-alkyne "click" cycloaddition monitored by real time infrared spectroscopy. Journal of Physical Chemistry A. ,vol. 114, pp. 8331- 8336 ,(2010) , 10.1021/JP105034M