[en] The palladium(ii) dimer, [Pd(C,N-C 6H 4CH 2NMe 2)Cl] 2 reacts with two equivalents of the NHC·CS 2 zwitterionic ligands [NHC = IPr (1,3- diisopropylimidazol-2-ylidene), ICy (1,3-dicyclohexylimidazol-2-ylidene), IMes (1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IDip (1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene), SIMes (1,3-bis(2,4,6-trimethylphenyl) imidazolin-2-ylidene)] in the presence of NH 4PF 6, to yield the cationic products [Pd(C,N-C 6H 4CH 2NMe 2)(S 2C·NHC)] +. In a similar fashion, the compounds [Pd(C,N-bzq)(S 2C·NHC)] + (bzq = benzo[h]quinolinyl, NHC = ICy, IMes, IDip) are obtained from the corresponding dimer [Pd(C,N-bzq)Cl] 2. The bis(phosphine) compounds [Pd(S 2C·NHC)(PPh 3) 2] 2+ (NHC = ICy, IMes, IDip, SIMes) are obtained on treatment of [PdCl 2(PPh 3) 2] with NHC·CS 2 zwitterions in the presence of NH 4PF 6. The reaction of [PdCl 2(dppf)] with IMes·CS 2 and NH 4PF 6 provides the complex [Pd(S 2C·IMes)(dppf)] 2+. The complexes [Pd(S 2C·NHC)(PPh 3) 2](PF 6) 2 (NHC = IMes, IDip) were active pre-catalysts (1 mol% loading) for the conversion of benzo[h]quinoline to 10-methoxybenzo[h]quinoline in the presence of PhI(OAc) 2 and methanol. The intermediacy of [Pd(C,N-bzq)(S 2C·NHC)] + was supported by the high yield of 10-methoxybenzo[h]quinoline using [Pd(C,N-bzq)(S 2C·IDip)] + to promote the same reaction. Small amounts of 2,10-dimethoxybenzo[h]quinoline were also isolated from these reactions. Using [Pd(C,N-bzq)(S 2C·IDip)] + and N-chlorosuccinimide as the oxidant led to the formation of 10-chlorobenzo[h]quinoline in moderate yield from benzo[h]quinoline. The molecular structures of [Pd(S 2C·IMes)(PPh 3) 2](PF 6) 2 and [Pd(S 2C·IMes) (dppf)](PF 6) 2 were determined crystallographically.
Disciplines :
Chemistry
Author, co-author :
Champion, Martin J. D.; Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom
Solanki, Riten; Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom
Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
White, Andrew J. P.; Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom
Wilton-Ely, James D. E. T.; Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, United Kingdom
Language :
English
Title :
Synthesis and catalytic application of palladium imidazol(in)ium-2- dithiocarboxylate complexes
Publication date :
2012
Journal title :
Dalton Transactions
ISSN :
1477-9226
eISSN :
1477-9234
Publisher :
Royal Society of Chemistry, Cambridge, United Kingdom
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