A novel tetramer copper(I) complex containing diallylphosphine ligands: Synthesis, characterization and catalytic application in A3-coupling (Aldehyde-Amine-Alkyne) reactions

[Display omitted] •A tetramer copper(I) complex with tert-butyldiallylphosphine has been synthesized and characterized.•Tetramer copper(I) complex shows a cubane-like structure in solid state.•Isomerization of tetramer copper(I) complex was observed in solution.•A3-Coupling (Aldehyde-Amine-Alkyne) R...

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Bibliographic Details
Published in:Inorganica Chimica Acta 2017-10, Vol.467, p.155-162
Main Authors: Rosales, Jennifer, Garcia, Juan M., Ávila, Edward, González, Teresa, Coll, David Santiago, Ocando-Mavárez, Edgar
Format: Article
Language:English
Subjects:
A3-coupling reactions
Aldehydes
Aliphatic compounds
Alkynes
Amines
Catalysis
Chemical reactions
Chemical synthesis
Coordination compounds
Copper chloride
Copper compounds
Coupling
Cubane
Diallylphosphine ligands
Isomerization
Ligands
NMR
Nuclear magnetic resonance
Propargylamine
Tetramer cobre(I) complex
X-ray diffraction
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Summary:[Display omitted] •A tetramer copper(I) complex with tert-butyldiallylphosphine has been synthesized and characterized.•Tetramer copper(I) complex shows a cubane-like structure in solid state.•Isomerization of tetramer copper(I) complex was observed in solution.•A3-Coupling (Aldehyde-Amine-Alkyne) Reaction catalyzed by tetramer copper(I) complex. A novel tetrameric copper(I) complex containing tert-butyldiallylphosphine ligands, [CuCl{tBu-P(CH2CH=CH2)2}]4 (2), has been synthesized and characterized by structural and spectroscopic methods. X-ray diffraction analysis showed that 2has a cubane-like solid structure of formula [CuCl{κ1(P)-tBu-P(CH2CH=CH2)2}]4. In solution, a dynamic behavior generated by the cubane⇄chair isomerization was detected by variable temperature NMR analysis. DFT calculations have been performed to explain the observed dynamic equilibrium in solution. The use of copper(I) complex 2 as catalyst for the synthesis of propargylamines via A3-coupling reactions has been tested. Complex 2 is capable of promoting A3-coupling reactions of both aromatic and aliphatic aldehydes with cyclic secondary amines and phenylacetylene. The reaction proceeds under mild condition and absence of solvent.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2017.07.038