Pd-catalyzed coupling reactions of 1,1-dibromo-1-alkenes with various arylboronic acids in Aqueous Solution

Effective Palladium-Catalyzed Synthesis of Triarylethene-Based Molecules in Aqueous Solution
Yan Zhu, et al
DOI: 10.1002/ejoc.201200577

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201200577/abstract

 Highly effective and selective Pd-catalyzed coupling reactions of 1,1-dibromo-1-alkenes with various arylboronic acids have been performed in aqueous solution under mild conditions. The method is simple, economic, and practical for the synthesis of triarylethene-based compounds.

   Thumbnail image of graphical abstract

General procedure for Pd-catalyzed double coupling between various 1,1-dihalo-

1-alkenes and arylboronic acids without using ligand:

1,1-Dihalo-1-alkene (0.3 mmol) was dissolved in the mixed solvent (PEG-400, 0.5

mL and H2O 1.5 mL), followed by addition of arylboronic acid (0.7 mmol), palladium

acetate (0.012 mmol), potassium phosphate (0.6 mmol), The reaction mixture was

stirred at 40 oC for 24 h. After cooling to room temperature, the mixture was diluted

with water, and the combined aqueous phases were extracted three times with ethyl

acetate. The organic layers were combined, dried over Na2SO4, and concentrated to

yield the crude product, which was further purified by silica gel chromatography,

using petroleum ether and ethyl acetate as eluent to provide the desired product. 

References:

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Korotchenko, A. V. Shastin, E. S. Balenkova, J. Chem. Soc.; Perkin Trans.1 2002,

1883-887; c) V. N. Korotchenko, A. V. Shastin, E. S. Balenkova, Org. Biomol. Chem

2003, 1, 1906-1908; d) G. T. Hwang, H. S. Son, J. K. Ku, B. H. Kim, J. Am. Chem.

Soc. 2003, 125, 11241-11248.

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