Sterically hindered selenoether ligands: Palladium(ii) complexes as catalytic activators for Suzuki-Miyaura coupling

Umesh Kumar, Pooja Dubey, Ved Vati Singh, Om Prakash, Ajai K. Singh

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

2-Hydroxy/(benzyloxy)-3,5-di-tert-butyl benzaldehyde reacts with PhSeCH2CH2NH2resulting in a sterically hindered selenoether ligand (Schiff base) [2-HO-3,5-(C(CH3)3)2-C6H2-CN-(CH2)2SePh] (L1)/[2-PhCH2O-3,5-(C(CH3)3)2-C6H2-CH2-NH-(CH2)2SePh] (L2). The reactions of L1 and L2 with Na2PdCl4in methanol and acetone-water mixture at room temperature have resulted in complexes [PdCl (L1-H)] (1) and [PdCl2(L2)] (2)], respectively. Both the complexes and their ligands have been characterized with 1H, 13C{1H} and 77Se{1H} NMR spectroscopy. The molecular structures of complexes 1 and 2 have been determined with single crystal X-ray diffraction. The Pd-Se bond lengths in 1 and 2 are 2.370(1) and 2.366(1) Å, respectively. The geometry around palladium in both the complexes is nearly square planar. Complexes 1 and 2 (0.1 mol% Pd) have been found efficient as catalysts for Suzuki-Miyaura C-C coupling reactions in the presence of K2CO3in ethanol. The catalysis in water with complex 1 in the presence of K2CO3was found feasible but with low conversion (up to 40%). The efficiency of 1 in carrying out the coupling is marginally better than that of 2.

Original languageEnglish
Pages (from-to)41659-41665
Number of pages7
JournalRSC Advances
Volume40
Issue number78
DOIs
StatePublished - 1 Jan 2014
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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