Abstract

A new water soluble palladium(II) complex ( 2) derived from N, N, N′, N′-tetrakis(2-hydroxyethyl)ethylenediamine (edteH 4) ( 1) was synthesized in high yield and characterized by 1H, 13C, HMQC and COSY NMR spectroscopy. X-ray diffraction studies on a single crystal of 2 confirmed the cis square planar geometry; the edteH 4 ligand ( 1) is κ 2 (N,N)-coordinated with four pendant CH 2CH 2OH groups. This new complex [PdCl 2(edteH 4)] ( 2) and the previously synthesized triethanolamine complex [Pd(OCH 2CH 2N(CH 2CH 2OH) 2) 2] ( 3) were tested as catalysts for the Suzuki/Miyaura cross-coupling reaction of various aryl bromides with phenylboronic acid in water. Electronically activated aryl bromides, such as 4-bromoacetophenone and 4-bromobenzaldehyde undergo the cross-coupling with extremely high turnover numbers (TON) of up to 1,00,000 without organic solvent.

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