Role of Halide Ions in Divalent Palladium-Mediated Reactions: Competition between β-Heteroatom Elimination and β-Hydride Elimination of a Carbon−Palladium Bond

Role of Halide Ions in Divalent Palladium-Mediated Reactions: Competition between β-Heteroatom Elimination and β-Hydride Elimination of a Carbon−Palladium Bond
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DOI:
10.1021/om0101994
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发表时间:
2001-07
期刊:
影响因子:
2.8
通讯作者:
Zhaoguo Zhang;Xiyan Lu;Zhen-Jiang Xu;A. Zhang;Xiuling Han
Zhaoguo Zhang;Xiyan Lu;Zhen-Jiang Xu;A. Zhang;Xiuling Han
中科院分区:
化学2区
文献类型:
--
作者:
Zhaoguo Zhang;Xiyan Lu;Zhen-Jiang Xu;A. Zhang;Xiuling Han

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The integral role of halide ions as a ligand in the reactions of stoichiometric arylpalladium reagents and Pd(II)-catalyzed reaction of phenylmercuric acetate with various allylic compounds were studied. The halide ion was found to inhibit β-H elimination and promote β-heteroatom elimination in acidic media. In this reaction, a C−Pd intermediate with a β-heteroatom (including halogen, acetoxy, alkoxy, and hydroxyl groups) gives only β-heteroatom elimination product in the presence of halide ions, while β-H elimination is effectively blocked.