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通过电化学氧化实现钯催化的芳烃C-H与卤化氢的卤化反应。

Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation.

作者信息

Kakiuchi Fumitoshi, Kochi Takuya, Mutsutani Hitoshi, Kobayashi Noboru, Urano Seiya, Sato Mitsuo, Nishiyama Shigeru, Tanabe Takamasa

机构信息

Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.

出版信息

J Am Chem Soc. 2009 Aug 19;131(32):11310-1. doi: 10.1021/ja9049228.

Abstract

A new strategy for catalytic functionalization of C-H bonds by means of electrochemical oxidation is described. Combination of palladium-catalyzed aromatic C-H bond cleavage and halogenation with electrochemically generated halonium ions enables highly efficient, selective halogenations of aromatic compounds in a green-sustainable manner. The required reagents for this reaction are an arene and an aqueous hydrogen halide as substrates, a palladium salt as a catalyst, and an organic solvent. No further additives such as electrolytes, oxidants, or ligands are necessary to achieve effective catalytic activity. Several remarkable advantages of the use of the electrochemical method are also described.

摘要

描述了一种通过电化学氧化实现C-H键催化官能化的新策略。钯催化的芳香族C-H键裂解与电化学生成的卤鎓离子的卤化反应相结合,能够以绿色可持续的方式对芳香族化合物进行高效、选择性卤化。该反应所需的试剂为芳烃和卤化氢水溶液作为底物、钯盐作为催化剂以及有机溶剂。无需其他添加剂(如电解质、氧化剂或配体)即可实现有效的催化活性。还描述了使用电化学方法的几个显著优点。

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