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Synlett 2013; 24(10): 1255-1259
DOI: 10.1055/s-0033-1338848
DOI: 10.1055/s-0033-1338848
cluster
Synthesis of Novel N-Heterocyclic Carbene-Oxazoline Palladium Complexes and Their Applications in Suzuki–Miyaura Cross-Coupling Reaction
Further Information
Publication History
Received: 18 April 2013
Accepted after revision: 02 May 2013
Publication Date:
17 May 2013 (online)
Abstract
A series of novel N-heterocyclic carbene-oxazoline ligands were synthesized in six steps. Palladium complexes were obtained by deprotonation of the benzimidazole salts and subsequent ligation with Pd(OAc)2 in THF. Different types of cyclic bis- and tetrapalladium complexes were achieved by modifying substituent of oxazoline group. The structures of these palladium complexes were characterized by NMR and X-ray diffraction analysis. Catalytic properties of these Pd-complexes were tested by Suzuki–Miyaura cross-coupling reaction.
Key words
N-heterocyclic carbene - oxazoline - palladium complex - Suzuki–Miyaura cross-coupling reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 19 General Procedure of the NHC-Pd Catalyzed Suzuki–Miyaura Cross-Coupling Reaction: NHC-Pd (1.25 or 2.5 μmol, 1 mol% Pd), aryl halide (0.5 mmol, 1 equiv), arylboronic aid (0.6 mmol, 1.2 equiv), potassium tert-butoxide (0.75 mmol, 1.5 equiv) were added into a tube under argon, and the solvent i-PrOH (2 mL) was added into the tube via a syringe. The mixture was stirred for 16 h at 80 °C. After the reaction completed, H2O was added to the mixture, and the aqueous phase was extracted with EtOAc (3 ×). The combined organic solvent was dried over anhyd Na2SO4 and removed in vacuo. The residue was purified by flash column chromatography on silica gel column with petroleum ether as an eluent to give the desired biaryl products 8 in good to excellent yields.