Issue 78, 2014

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

Abstract

2-Hydroxy/(benzyloxy)-3,5-di-tert-butyl benzaldehyde reacts with PhSeCH2CH2NH2 resulting in a sterically hindered selenoether ligand (Schiff base) [2–HO–3,5–(C(CH3)3)2–C6H2–C[double bond, length as m-dash]N–(CH2)2SePh] (L1)/[2–PhCH2O–3,5–(C(CH3)3)2–C6H2–CH2–NH–(CH2)2SePh] (L2). The reactions of L1 and L2 with Na2PdCl4 in 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 K2CO3 in ethanol. The catalysis in water with complex 1 in the presence of K2CO3 was 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.

Graphical abstract: Sterically hindered selenoether ligands: palladium(ii) complexes as catalytic activators for Suzuki–Miyaura coupling

Supplementary files

Article information

Article type
Paper
Submitted
27 Jun 2014
Accepted
28 Aug 2014
First published
28 Aug 2014

RSC Adv., 2014,4, 41659-41665

Sterically hindered selenoether ligands: palladium(II) complexes as catalytic activators for Suzuki–Miyaura coupling

U. Kumar, P. Dubey, V. V. Singh, O. Prakash and A. K. Singh, RSC Adv., 2014, 4, 41659 DOI: 10.1039/C4RA06313A

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