An Efficient and Selective Pd-catalyzed Dehalogenation Reaction

Author(s): Fu-Ling Xue, Ji Qi, Pai Peng, Guang-Zhen Mo, Zhao-Yang Wang.

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 1 , 2014

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Abstract:

During the research on the Pd-catalyzed intramolecular cyclization reaction via C-H activation, the dehalogenation of 3-halo-2(5H)-furanones is unexpectedly discovered. Under the optimized conditions without any special anaerobic and anhydrous treatments, using N,N-diisopropylethylamine (DIPEA) simultaneously as hydrogen source and base, the reactions of 27 substrates with less Pd catalyst (5 mol% Pd(PPh3)4) usually give higher yields (70-99%, mostly over 82%). Especially for 3-halo-2(5H)-furanone substrates simultaneously containing aryl halide structure, this kind of Pd-catalyzed dehalogenation has good selectivity. After the selectivity is explained via the substrate theoretical calculation, a possible reaction mechanism of the Pd-catalyzed dehalogenation is proposed. These novel investigations provide an efficient, simple, practical and selective Pd-catalyzed dehalogenation method for the non-aromatic halide substrates with many different functional groups.

Keywords: Amines, chemoselectivity, dehalogenation, 2(5H)-Furanone, halide, mass spectroscopy, palladium.

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Article Details

VOLUME: 11
ISSUE: 1
Year: 2014
Page: [64 - 79]
Pages: 16
DOI: 10.2174/15701786113109990041

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