Structurally Characterized Cationic Silver(I) and Ruthenium(II) Carbene Complexes of 1,2,3-Triazol-5-ylidenes

Cai, Jiajia; Yang, Xiaoping; Arumugam, Kuppuswamy; Bielawski, Christopher W.; Sessler, Jonathan L.

doi:10.1021/om200670f

Cited by 74 publications

(47 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 H NMR (CDCl 3 , 400 MHz): δ 7.67 (s, 2H, H trz ), 6.98 (s, 4H, H Mes ), 4.87 (s, 4H, OCH 2 ), 2.34 (s, 6H, CH 3-para ), 1.96 (s, 12H, CH 3-ortho ). 13 C{ 1 H} NMR (CDCl 3 , 100 MHz): δ 144.6 (C trz ), 140.1 (C para ) 135.2 (C ortho ), 133.5 (C ipso ), 129.2 (C meta ), 124.9 (C trz -H), 63.8 (OCH 2 ), 21.2 (CH 3-para ), 21;H,6.78;N,20.18%. Found: C,69.44;H,6.90;N,19.93%.…”

Section: General Procedures For the Synthesis Of Ditriazoles 3 Andmentioning

confidence: 99%

Versatile bonding and coordination modes of ditriazolylidene ligands in rhodium(iii) and iridium(iii) complexes

2016

View full text Add to dashboard Cite

Metalation of novel ditriazolium salts containing a trimethylene (-CHCHCH-) or dimethylether linker (-CHOCH-) was probed with different rhodium(iii) and iridium(iii) precursors. When using [MCp*Cl], a transmetalation protocol via a triazolylidene silver intermediate was effective, while base-assisted metalation with MClvia sequential deprotonation of the triazolium salt with KOtBu and addition of the metal precursor afforded homoleptic complexes. The N-substituent on the triazole heterocycle directed the metalation process and led to C,C,C-tridentate chelating ditriazolylidene complexes for N-phenyl substituents. With ethyl substituents, only C,C-bidentate complexes were formed, while metalation with mesityl substituents was unsuccessful, presumably due to steric constraints. Through modification of the reaction conditions for the metalation step, an intermediate species was isolated that contains a C,C-bidentate chelate en route to the formation of the tridentate ligand system. Accordingly, C-H bond activation occurs prior to formation of the second metal-triazolylidene bond. Stability studies with a C,C,C-tridentate chelating ditriazolylidene iridium complex towards DCl showed deuterium incorporation at both N-phenyl groups and indicate that C-H bond activation is reversible while the C-Ir bond is robust. The flexible linker between the two triazolylidene donor sites provides access to both facial and meridional coordination modes.

show abstract

Section: General Procedures For the Synthesis Of Ditriazoles 3 Andmentioning

confidence: 99%

Versatile bonding and coordination modes of ditriazolylidene ligands in rhodium(iii) and iridium(iii) complexes

2016

View full text Add to dashboard Cite

show abstract

“…16 The average Ag-C MIC bond length is 2.086(2) A and is comparable with previously reported values. 7,8 In proton NMR, the formation of 3(BF 4 ) 4 was accompanied by the disappearance of the triazolium-H and the methylene-H 2 signals (see ESI, S5 and S6 ‡). A set of four singlets is obtained, corresponding to four inequivalent methyl groups caused by the twisted geometry of 3(BF 4 ) 4 .…”

Section: Resultsmentioning

confidence: 99%

The transformations of a methylene-bridged bis-triazolium salt: a mesoionic carbene based metallocage and analogues of TCNE and NacNac

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[7i] Hence, not many examples of isolated silver complexes are known. The first structurally characterized silver complex was reported in 2011 . This complex turned out to be a cluster containing eight silver ions ( 132 ).…”

Section: Discussionmentioning

confidence: 99%

Metal Complexes of Click-Derived Triazoles and Mesoionic Carbenes: Electron Transfer, Photochemistry, Magnetic Bistability, and Catalysis

Schweinfurth

Hettmanczyk

Suntrup

et al. 2017

Z. Anorg. Allg. Chem.

162

104

View full text Add to dashboard Cite

Abstract. Even though the existence of 1,2,3-triazoles has been known for more than a century, the recent discovery of a copper(I) catalyzed version of this reaction has attributed unprecedented importance to these compounds. Coordination and organometallic chemists have benefited from this modular synthetic route, and have accessed ligands based on both the triazoles as well as the triazolylidenes. The wide variation of steric and electronic properties that can be achieved for this ligand class has made them useful for generating metal complexes

show abstract

Structurally Characterized Cationic Silver(I) and Ruthenium(II) Carbene Complexes of 1,2,3-Triazol-5-ylidenes

Cited by 74 publications

References 64 publications

Versatile bonding and coordination modes of ditriazolylidene ligands in rhodium(iii) and iridium(iii) complexes

Versatile bonding and coordination modes of ditriazolylidene ligands in rhodium(iii) and iridium(iii) complexes

The transformations of a methylene-bridged bis-triazolium salt: a mesoionic carbene based metallocage and analogues of TCNE and NacNac

Metal Complexes of Click-Derived Triazoles and Mesoionic Carbenes: Electron Transfer, Photochemistry, Magnetic Bistability, and Catalysis

Contact Info

Product

Resources

About