An Efficient and Selective Pd-catalyzed Dehalogenation Reaction

Title:An Efficient and Selective Pd-catalyzed Dehalogenation Reaction

Volume: 11 Issue: 1

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

Affiliation:

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

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.

Cite this article as:

Xue Fu-Ling, Qi Ji, Peng Pai, Mo Guang-Zhen and Wang Zhao-Yang, An Efficient and Selective Pd-catalyzed Dehalogenation Reaction, Letters in Organic Chemistry 2014; 11 (1) . https://dx.doi.org/10.2174/15701786113109990041