Synlett 2013; 24(10): 1255-1259
DOI: 10.1055/s-0033-1338848
cluster
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel N-Heterocyclic Carbene-Oxazoline Palladium Complexes and Their Applications in Suzuki–Miyaura Cross-Coupling Reaction

Peng Gu
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China
,
Qin Xu*
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China
,
Min Shi*
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China
b  State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: mshi@mail.sioc.ac.cn
› Author Affiliations
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.

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.