Synlett 2008(20): 3239-3241  
DOI: 10.1055/s-0028-1087368
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Propylene Oxide Assisted Sonogashira Coupling Reaction

Zhaolong Tonga, Peng Gaoa,b, Haibing Denga, Lei Zhanga, Peng-Fei Xub, Hongbin Zhai*a,b
a Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
b State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China
Fax: +86(21)64166128; e-Mail: zhaih@mail.sioc.ac.cn;
Further Information

Publication History

Received 5 June 2008
Publication Date:
26 November 2008 (online)

Abstract

A propylene oxide assisted base-free Sonogashira cross-coupling reaction has been developed. The unique feature of the current protocol has extended the scope of Sonogashira reaction to some base-sensitive substrates.

    References and Notes

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    General Procedure: The Batey Pd-carbene complex 1 (2.5 mol%), CuI (5 mol%), Ph3P (2.5 mol%) and DMF (2 mL) were added to a dry 10-mL septum-capped round-bottomed flask under a nitrogen atmosphere. Aryl iodide (2 mmol), alkyne (110 mol%), and PO (5 equiv) were then added to the above mixture. While the mixture was stirred, the flask was cooled to -78 ˚C, vacuumed, and charged with nitrogen. This process was repeated for three times. After the mixture was warmed to 25 ˚C, stirring was continued at that temperature for 48 h. The mixture was diluted with H2O and extracted with E2O. The organic extracts were combined, washed with brine, dried (MgSO4), filtered, and concentrated to give a residue, which was purified by flash column chromatography on silica gel.

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