Efficient Ni(II)2Ln(III)2 Electrocyclization Catalysts for the Synthesis of trans-4,5-Diaminocyclopent-2-enones from 2-Furaldehyde and Primary or Secondary Amines

Kieran Griffiths; Prashant Kumar; James D Mattock; Alaa Abdul-Sada; Mateusz B Pitak; Simon J Coles; Oscar Navarro; Alfredo Vargas; George E Kostakis

doi:10.1021/acs.inorgchem.6b00720

Efficient Ni(II)2Ln(III)2 Electrocyclization Catalysts for the Synthesis of trans-4,5-Diaminocyclopent-2-enones from 2-Furaldehyde and Primary or Secondary Amines

Inorg Chem. 2016 Jul 18;55(14):6988-94. doi: 10.1021/acs.inorgchem.6b00720. Epub 2016 Jun 29.

Authors

Kieran Griffiths¹, Prashant Kumar¹, James D Mattock¹, Alaa Abdul-Sada¹, Mateusz B Pitak², Simon J Coles², Oscar Navarro¹, Alfredo Vargas¹, George E Kostakis¹

Affiliations

¹ Department of Chemistry, School of Life Sciences, University of Sussex , Brighton BN1 9QJ, United Kingdom.
² UK National Crystallography Service, Chemistry, University of Southampton , Highfield Campus, Southampton, SO17 1BJ, United Kingdom.

PMID: 27355452
DOI: 10.1021/acs.inorgchem.6b00720

Abstract

A series of heterometallic coordination clusters (CCs) [Ni(II)2Ln(III)2(L1)4Cl2(CH3CN)2] 2CH3CN [Ln = Y (1Y), Sm (1Sm), Eu (1Eu), Gd (1Gd), or Tb (1Tb)] were synthesized by the reaction of (E)-2-(2-hydroxy-3-methoxybenzylidene-amino)phenol) (H2L1) with NiCl2·6(H2O) and LnCl3·x(H2O) in the presence of Et3N at room temperature. These air-stable CCs can be obtained in very high yields from commercially available materials and are efficient catalysts for the room-temperature domino ring-opening electrocyclization synthesis of trans-4,5-diaminocyclopent-2-enones from 2-furaldehyde and primary or secondary amines under a non-inert atmosphere. Structural modification of the catalyst to achieve immobilization or photosensitivity is possible without deterioration in catalytic activity.