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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Selective functionalization of C(sp3)-H bonds: catalytic chlorination and bromination by IronIII-acacen-halide under
Chang Shen1, Wasihun Menberu Dagnaw2, Ching Wai Fong1
1Department of Science and Environmental Studies, The Education University of Hong Kong, 10 Lo Ping Road, Tai Po, Hong Kong SAR, China. cfchow@eduhk.hk.
Abstract:
The oxidative catalytic halogenations of the C(sp3)-H bond of alkanes promoted by FeIII(acacen)Cl (1III-Cl) and FeIII(acacen)Br (1III-Br) in the presence of trifluoroacetic acid (TFA) were investigated. Four major steps were involved: (i) formation of [FeV(acacen)(oxo)X] species (X = Cl or Br), (ii) hydrogen-atom transfer, (iii) halogen atom rebound, and (iv) regeneration of 1III-Cl or 1III-Br. TFA played a significant role in (i) forming the high-valent iron-oxo intermediate and (ii) generating the reaction selectivity.
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