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Synthesis, characterisation and reactivity of copper(I) amide complexes and studies on their role in the modified Ullmann amination reaction.

Sung S, Braddock DC, Armstrong A, Brennan C, Sale D, White AJ, Davies RP - Chemistry (2015)

Bottom Line: Complexes 1, 2 and 4 are shown to exist as tetramers in the solid state by X-ray crystallography.In [D6 ]benzene solution, complexes 1, 2 and 5 were found by using (1) H DOSY NMR to exist in rapid equilibrium between aggregates with average aggregation numbers of 2.5, 2.4 and 3.3, respectively, at 0.05 M concentration.The role of phenanthroline has also been explored both in the stoichiometric reaction and in the catalytic Ullmann protocol.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ (UK).

No MeSH data available.


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Synthesis of copper(I) amide complexes 1–5.
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fig09: Synthesis of copper(I) amide complexes 1–5.

Mentions: The amines studied herein (dicyclohexylamine, tetramethylpiperidine (TMP), pyrrolidine, piperidine and benzylamine) were chosen to provide a range of steric bulk and also display varied performance in the catalytic coupling reaction, with primary amines known to provide better yields and reaction rates than acyclic secondary amines.[14] The copper amide complexes were prepared from the parent amines either via the lithium amide complex (Route A, Scheme 3) or by direct reaction of the amine with copper(I) mesityl (CuMes, Route B, Scheme 3).


Synthesis, characterisation and reactivity of copper(I) amide complexes and studies on their role in the modified Ullmann amination reaction.

Sung S, Braddock DC, Armstrong A, Brennan C, Sale D, White AJ, Davies RP - Chemistry (2015)

Synthesis of copper(I) amide complexes 1–5.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4471577&req=5

fig09: Synthesis of copper(I) amide complexes 1–5.
Mentions: The amines studied herein (dicyclohexylamine, tetramethylpiperidine (TMP), pyrrolidine, piperidine and benzylamine) were chosen to provide a range of steric bulk and also display varied performance in the catalytic coupling reaction, with primary amines known to provide better yields and reaction rates than acyclic secondary amines.[14] The copper amide complexes were prepared from the parent amines either via the lithium amide complex (Route A, Scheme 3) or by direct reaction of the amine with copper(I) mesityl (CuMes, Route B, Scheme 3).

Bottom Line: Complexes 1, 2 and 4 are shown to exist as tetramers in the solid state by X-ray crystallography.In [D6 ]benzene solution, complexes 1, 2 and 5 were found by using (1) H DOSY NMR to exist in rapid equilibrium between aggregates with average aggregation numbers of 2.5, 2.4 and 3.3, respectively, at 0.05 M concentration.The role of phenanthroline has also been explored both in the stoichiometric reaction and in the catalytic Ullmann protocol.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ (UK).

No MeSH data available.


Related in: MedlinePlus