Mechanisms for (porphyrinato) iron(III)-catalyzed oxygenation of styrenes by O2 in presence of BH4/-

Masayuki Takeuchi, Masahito Kodera, Koji Kano, Zen Ichi Yoshida

研究成果: Article査読

28 被引用数 (Scopus)


Mechanisms have been proposed for the (porphyrinato)iron(III)-catalyzed oxidation of styrene and α-methylstyrene by O2 in benzene-ethanol containing NaBH4. The product analysis and the deuterium incorporation using NaBD4 suggest that the (σ-alkyl)Fe(III)-Por complex, [C6H5CH(CH3)]Fe(III)-Por, is formed as an intermediate in the reaction of styrene. Insertion of O2 to the (σ-alkyl)Fe(III)-Por complex having a radical character yields a (peroxy)iron(III) complex, [C6H5CH(CH3)OO]Fe(III)-Por. The homolytic fission of the O-O bond followed by the hydrogen abstraction within the radical pair affords acetophenone and (HO)Fe(III)-Por. Acetophenone is readily reduced with NaBH4 to give 1- phenylethanol. Meanwhile, the reaction of α-methylstyrene with BH4 in the presence of Por-Fe(III)Cl may also yield the (σ-alkyl)Fe(III)-Por complex, which takes up O2 to form a (peroxy)iron(III) complex, (C6H5C(CH3)2OO)Fe(III)-Por. The (peroxy)iron(III) complex is directly reduced by BH4/- to give 2 phenyl-2-propanol and (HO)Fe(III)-Por. In the reaction of styrene, such direct reduction of the (peroxy)iron(III) complex as a minor pathway competes with the homolytic fission of its O-O bond.

ジャーナルJournal of Molecular Catalysis A: Chemical
出版ステータスPublished - 1996 11 25

ASJC Scopus subject areas

  • 触媒
  • プロセス化学およびプロセス工学
  • 物理化学および理論化学


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