Intermolecular C-C Coupling between 1-Methyl-1,2,3-Triazole and 2,2'-Bipyridine or 1,10-Phenanthroline in MoII Complexes.

Unsupported 1-methyl-1,2,3-triazole has been coordinated to {Mo(η3 -methallyl)(CO)2 (N-N)} (N-N=2,2'-bipyridine, bipy; or 1,10-phenanthroline, phen) fragments, yielding cationic complexes that can be regarded as metalated triazolium salts. Their reactivity towards a strong base led to the deprotonation of the C5-H group of the triazole moiety, followed by an intermolecular nucleophilic attack to the ortho CH group of a bipy or phen ligand affording cyclic, bimetallic dearomatized C-C coupling products. The reaction of the neutral bipy derivative with an acid led to the formation of dihydropyridyl units by protonation of a CH group of the dearomatized rings, the dimeric nature of complexes being mantained upon protonation.

[1]  B. Sarkar,et al.  Metal Complexes of Click‐Derived Triazoles and Mesoionic Carbenes: Electron Transfer, Photochemistry, Magnetic Bistability, and Catalysis , 2017 .

[2]  Julio Pérez,et al.  Interligand C-C Coupling between α-Methyl N-Heterocycles and bipy or phen at Rhenium Tricarbonyl Complexes. , 2017, Inorganic chemistry.

[3]  J. Crowley,et al.  Functional metallosupramolecular architectures using 1,2,3-triazole ligands: it's as easy as 1,2,3 "click". , 2017, Dalton transactions.

[4]  Brian M Zeglis,et al.  Click Chemistry and Radiochemistry: The First 10 Years. , 2016, Bioconjugate chemistry.

[5]  R. López,et al.  Activation of Aromatic C-C Bonds of 2,2'-Bipyridine Ligands. , 2016, Chemistry.

[6]  R. López,et al.  Influence of the N-N Coligand: C-C coupling instead of formation of imidazol-2-yl complexes at {Mo(η(3)-allyl)(CO)2} fragments. Theoretical and experimental studies. , 2015, Inorganic chemistry.

[7]  Julio Pérez,et al.  Deprotonation of coordinated phosphanes in a rhenium complex: C-C coupling with diimine coligands. , 2015, Chemistry.

[8]  D. Astruc,et al.  Catalysis by 1,2,3-triazole- and related transition-metal complexes , 2014 .

[9]  Jonathan A. Kitchen,et al.  The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry. , 2014, Chemical Society reviews.

[10]  Paul I. P. Elliott.  Chapter 1:Organometallic complexes with 1,2,3-triazole-derived ligands , 2014 .

[11]  Ulrich S Schubert,et al.  Beyond click chemistry - supramolecular interactions of 1,2,3-triazoles. , 2014, Chemical Society reviews.

[12]  Julio Pérez,et al.  Imidazole-nitrile or imidazole-isonitrile C-C coupling on rhenium tricarbonyl complexes. , 2013, Chemistry.

[13]  U. Bunz,et al.  Click to bind: metal sensors. , 2013, Chemistry, an Asian journal.

[14]  Christiane A. Kluba,et al.  Click-to-Chelate: Development of Technetium and Rhenium-Tricarbonyl Labeled Radiopharmaceuticals , 2013, Molecules.

[15]  M. Albrecht,et al.  Application of 1,2,3-triazolylidenes as versatile NHC-type ligands: synthesis, properties, and application in catalysis and beyond. , 2013, Chemical communications.

[16]  Julio Pérez,et al.  Re-mediated C-C coupling of pyridines and imidazoles. , 2012, Journal of the American Chemical Society.

[17]  O. Roubeau.  Triazole-based one-dimensional spin-crossover coordination polymers. , 2012, Chemistry.

[18]  L. García-Escudero,et al.  Beyond click chemistry: spontaneous C-triazolyl transfer from copper to rhenium and transformation into mesoionic C-triazolylidene carbene. , 2012, Chemical communications.

[19]  M. Drees,et al.  N-Heterocyclic carbenes via abstraction of ammonia: 'normal' carbenes with 'abnormal' character. , 2012, Chemical communications.

[20]  Lei Zhu,et al.  Structurally diverse copper(II) complexes of polyaza ligands containing 1,2,3-triazoles: site selectivity and magnetic properties. , 2012, Inorganic chemistry.

[21]  M. Botoshansky,et al.  1,2,3-Triazolylidene based complexes via post-modification of pincer click ligands. , 2011, Dalton transactions.

[22]  R. López,et al.  Imidazole to NHC rearrangements at molybdenum centers: an experimental and theoretical study. , 2011, Chemistry.

[23]  Paul I. P. Elliott,et al.  Synthesis and characterisation of luminescent rhenium tricarbonyl complexes with axially coordinated 1,2,3-triazole ligands. , 2011, Dalton transactions.

[24]  L. Bogani,et al.  Cobalt complexes with "Click"-derived functional tripodal ligands: spin crossover and coordination ambivalence. , 2011, Inorganic chemistry.

[25]  M. Todd,et al.  Chemical sensors that incorporate click-derived triazoles. , 2011, Chemical Society reviews.

[26]  O. Roubeau,et al.  Triazoles and tetrazoles: Prime ligands to generate remarkable coordination materials , 2011 .

[27]  Rajadurai Chandrasekar,et al.  "Super hybrid tridentate ligands": 4-substituted-2-(1-butyl-1H-1,2,3-triazol-4-yl)-6-(1H-pyrazol-1-yl)pyridine ligands coordinated to Fe(ii) ions display above room temperature spin transitions. , 2010, Dalton transactions.

[28]  S. García‐Granda,et al.  On the existence of an N-Metalated N-Heterocyclic carbene: A theoretical study , 2010 .

[29]  R. López,et al.  Effect of the nature of the substituent in N-alkylimidazole ligands on the outcome of deprotonation: ring opening versus the formation of N-heterocyclic carbene complexes. , 2010, Chemistry.

[30]  I. Turel,et al.  Click-triazole N2 coordination to transition-metal ions is assisted by a pendant pyridine substituent. , 2010, Inorganic chemistry.

[31]  J. Crowley,et al.  Use of di-1,4-substituted-1,2,3-triazole "click" ligands to self-assemble dipalladium(II) coordinatively saturated, quadruply stranded helicate cages. , 2010, Dalton transactions.

[32]  R. Schibli,et al.  Metal chelating systems synthesized using the copper(I) catalyzed azide-alkyne cycloaddition. , 2010, Dalton transactions.

[33]  M. Albrecht,et al.  1,2,3-Triazolylidenes as versatile abnormal carbene ligands for late transition metals. , 2008, Journal of the American Chemical Society.

[34]  Morten Meldal,et al.  Cu-catalyzed azide-alkyne cycloaddition. , 2008, Chemical reviews.

[35]  Guochen Jia,et al.  Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism. , 2008, Journal of the American Chemical Society.

[36]  D. Astruc,et al.  Synthesis and coordination chemistry of ferrocenyl-1,2,3-triazolyl ligands. , 2008, Inorganic chemistry.

[37]  Julio Pérez,et al.  Pyridine ring opening at room temperature at a rhenium tricarbonyl bipyridine complex. , 2008, Journal of the American Chemical Society.

[38]  A. Spek,et al.  "Click" 1,2,3-triazoles as tunable ligands for late transition metal complexes. , 2007, Dalton transactions.

[39]  D. Font,et al.  Assessing the suitability of 1,2,3-triazole linkers for covalent immobilization of chiral ligands: application to enantioselective phenylation of aldehydes. , 2007, The Journal of organic chemistry.

[40]  R. Schibli,et al.  "Click to chelate": synthesis and installation of metal chelates into biomolecules in a single step. , 2006, Journal of the American Chemical Society.

[41]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[42]  Morten Meldal,et al.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. , 2002, The Journal of organic chemistry.

[43]  I. Hachiya,et al.  Asymmetric Molybdenum-Catalyzed Alkylations , 1998 .

[44]  B. Trost,et al.  MOLYBDENUM CATALYSTS FOR ALLYLIC ALKYLATION , 1982 .

[45]  R. Huisgen.  1,3-Dipolar Cycloadditions. Past and Future† , 1963 .

[46]  R. Huisgen.  1.3‐Dipolare Cycloadditionen Rückschau und Ausblick , 1963 .

[47]  D. A. McMorran,et al.  “Click-Triazole” Coordination Chemistry: Exploiting 1,4-Disubstituted-1,2,3-Triazoles as Ligands , 2012 .

[48]  A. Gautier,et al.  Click Chelators for Platinum‐Based Anticancer Drugs , 2008 .