Synthesis of Dichlorobis(1,4-dimesityl-1<i>H</i>-1,2,3-triazol-5-ylidene)palladium [PdCl2(TMes)2] and Its Application to Suzuki–Miyaura Coupling Reaction

Nakamura, Tatsuhito; Ogata, Kenichi; Fukuzawa, Shin‐ichi

doi:10.1246/cl.2010.920

Cited by 67 publications

(44 citation statements)

References 28 publications

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“…In most cases the formation of the silver carbene is surmised, using NMR spectroscopy, by the disappearance of the low field 19,36,37 Both forms exist as syn and anti conformers. 36 However, performing the carbene transfer in the presence of NaI selectively yields the dimeric palladium species, 22, with bridging iodide groups.…”

Section: Synthesis Of 124-substituted 123-triazolylidene Precursorsmentioning

confidence: 99%

“…Specifically, the enhanced donor properties of 60 triazolylidenes compared to phosphines and C2-bound imidazolylidenes, is expected to promote the oxidative arylhalide addition to the palladium (0) Adaptation of the wingtip groups of the triazolylidene ligand to mesityl substituents (complex trans-21a) increases the catalytic activity and allows less reactive arylchlorides to be crosscoupled. 37 19 bearing a 'throw-away' ligand have been investigated in Suzuki-Miyaura catalysis. A series of (substituted) allyl complexes 18 have been reported by Fukuzawa et al to catalyse arylation of arylchlorides at room temperature.…”

Section: Catalysismentioning

confidence: 99%

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Application of 1,2,3-triazolylidenes as versatile NHC-type ligands: synthesis, properties, and application in catalysis and beyond

2013

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Triazolylidenes have rapidly emerged as a powerful subclass of N-heterocyclic carbene ligands for transition metals. They are readily available through regioselective [2+3] cycloaddition of alkynes and azides and subsequent metallation according to procedures established for related carbenes. Due to their mesoionic character, triazolylidenes are stronger donors than Arduengo-type imidazol-2-ylidenes. Spurred by these attractive attributes and despite their only recent emergence, triazolylidenes have shown 10 major implications in catalysis. This feature article summarises the synthetic accessibility of triazolylidene metal complexes and their electronic and structural characteristics, and it compiles their applications, in particular, as catalyst precursors for various bond forming and redox reactions, as well as first approaches into photophysical and biochemical domains.

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Section: Synthesis Of 124-substituted 123-triazolylidene Precursorsmentioning

confidence: 99%

Section: Catalysismentioning

confidence: 99%

Application of 1,2,3-triazolylidenes as versatile NHC-type ligands: synthesis, properties, and application in catalysis and beyond

2013

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“…1 and Scheme 1), respectively [26–27]. Treatment of 1,4-dimesityl-3-methyl-1,2,3-triazolium iodide with freshly prepared silver oxide followed by transmetalation with Pd(Cl) 2 (CH 3 CN) 2 yielded 1 as a pale yellow solid in 87% (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…Although the synthesis of 1 was reported by Fukuzawa [27] the crystal structure of this complex was not reported. Slow evaporation of an acetonitrile solution of 1 yielded single crystals suitable for X-ray crystallography.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

Shaik¹,

Ramkumar²,

Varghese³

et al. 2013

Beilstein J. Org. Chem.

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Summary trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki–Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and with high turnover numbers. With 1,4-dibromobenzene the catalyst was found to be active for up to 13 consecutive cycles with a turnover number of 1260. The polyarylarenes were obtained in pure form after crystallization once without recourse to chromatographic purification. The single-crystal X-ray structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl-1,2,3-triazol-5-ylidene as the ligand.

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Helical Poly(quinoxaline‐2,3‐diyl)s Bearing 1,2,3‐Triazole Pendants: Synthesis by CuAAC and Use as Reusable Abnormal NHC Ligands in Gold Catalysis

2018

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Poly(quinoxaline‐2,3‐diyl)s (PQXs) bearing 1,2,3‐triazole pendants were synthesized by living copolymerization of achiral 1,2‐diisocyanobenzenes or by post‐polymerization functionalization of PQXs bearing alkyne pendants through copper‐catalyzed azide–alkyne cycloaddition. Thus prepared PQXs bearing 1,2,3‐triazole pendants were treated with MeI, Ag2O, and AuCl successively, giving polymer‐supported gold complexes bearing 1,2,3‐triazolylidenes as abnormal N‐heterocyclic carbene (aNHC) ligands. The polymer‐based aNHC ligand served as a catalyst for the reaction of styrene with a propargylic ester to form a cyclopropane derivative. The catalyst could be reused at least eight times without loss of activity.

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Synthesis of Dichlorobis(1,4-dimesityl-1H-1,2,3-triazol-5-ylidene)palladium [PdCl2(TMes)2] and Its Application to Suzuki–Miyaura Coupling Reaction

Abstract: Novel catalyst containing an abnormal NHC ligand shows high activity in the Suzuki—Miyaura as well as Mizoroki—Heck reactions.

Cited by 67 publications

References 28 publications

Application of 1,2,3-triazolylidenes as versatile NHC-type ligands: synthesis, properties, and application in catalysis and beyond

Application of 1,2,3-triazolylidenes as versatile NHC-type ligands: synthesis, properties, and application in catalysis and beyond

Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

Helical Poly(quinoxaline‐2,3‐diyl)s Bearing 1,2,3‐Triazole Pendants: Synthesis by CuAAC and Use as Reusable Abnormal NHC Ligands in Gold Catalysis

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