2001
DOI: 10.1002/1099-0690(200112)2001:23<4479::aid-ejoc4479>3.0.co;2-0
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Difunctional Pyrazole Derivatives − Key Compounds en Route to Multidentate Pyrazolate Ligands

Abstract: Straightforward syntheses for some basic functional pyrazole derivatives are reported. These compounds serve as starting materials for the preparation of a series of new 3,5-donorsubstituted multifunctional pyrazole compounds, which may act as compartmental dinucleating ligand scaffolds for the controlled assembly of bimetallic complexes. The thp-protected 3,5-bis(chloromethyl)pyrazole (1), and in particular the more reactive 3,5-bis(bromomethyl) analogue 3, permit efficient attachment of various N-donor side … Show more

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Cited by 41 publications
(7 citation statements)
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“…NHC-(CH 2 ) n -functionalized fluorenyl complexes of metals have also been known [21]. Nitrogen or other heteroatom-donor side chain-functionalized pyrazolates can serve as polydentate ligands, and a pyrazol-1-yl tethered to a Cp ligand might also serve as an intramolecular function as a chelate donor in metal complexes [23][24][25][26]. Bis(cyclopentadienyl)-fuctionalized pyrazoles (H 3 L), i.e., 3,5-bis(fluoren-9-ylmethyl)-1H-pyrazole and 3,5-bis(inden-3-ylmethyl)-1H-pyrazole, and their lithium salts (Li 3 L) were synthesized [27] (Chart 1).…”
Section: Introductionmentioning
confidence: 58%
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“…NHC-(CH 2 ) n -functionalized fluorenyl complexes of metals have also been known [21]. Nitrogen or other heteroatom-donor side chain-functionalized pyrazolates can serve as polydentate ligands, and a pyrazol-1-yl tethered to a Cp ligand might also serve as an intramolecular function as a chelate donor in metal complexes [23][24][25][26]. Bis(cyclopentadienyl)-fuctionalized pyrazoles (H 3 L), i.e., 3,5-bis(fluoren-9-ylmethyl)-1H-pyrazole and 3,5-bis(inden-3-ylmethyl)-1H-pyrazole, and their lithium salts (Li 3 L) were synthesized [27] (Chart 1).…”
Section: Introductionmentioning
confidence: 58%
“…However, in our cases, reactions of nickelocene with 7, 8, 13, 16 or 18 under mild (room temperature) or relatively harsh (in refluxing toluene) conditions only yielded trimetallic complexes of type [CpNi{4-(Ind-(CH 2 ) n )-RR 0 Pz} 2 ] 2 Ni (20)(21)(22)(23)(24) These results are attributed to the bulkier hindrance of the 3,5-diphenyl groups on the pyrazolyl ring of 19 than that of the Pz-3,5-disubstituents in other indenyl-pyrazoles. Attempt to prepare and isolate the desired product analogous to complexes 20-24 or 25 from the reaction of Cp 2 Ni and 14 was unsuccessful.…”
Section: Synthesis Of Complexes 20-25mentioning
confidence: 99%
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“…These should be amenable via high-yielding and straightforward syntheses, which is particularly true for N-unsubstituted pyrazoles. 7,8 Established pyrazole building blocks include dialdehyde A 9 and diacid dichloride B 10 as well as diester C 11 (Figure1), all of which have proven useful for the preparation of, for example, macrocycles and multidentate ligand scaffolds incorporating one or more pyrazole moieties. 3 In order to broaden the scope of these systems, we set out to develop efficient syntheses for a variety of new 1H-pyrazole derivatives related to A-C with carbonyl or ester groups in the 3-and 5-positions, but with different substitution pattern both at the pyrazole-C4 position and the side arm carbonyl functions.…”
mentioning
confidence: 99%
“…Die Einf¸hrung des Cp-Grundkˆrpers in die Seitenarme funktionalisierter Pyrazolderivate wie 1 [5] erwies sich als unerwartet schwierig. Zur Synthese wurde das πgesch¸tzte™ Cp-Derivat [CpMn(CO) 3 ] in einer [Pd(PPh 3 ) 2 ]/ZnCl 2 -katalysierten Kreuzkupplung [6] mit dem Pyrazolkern unter Bildung von 2 verkn¸pft (Schema 1).…”
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