Iron(II)-Catalyzed Heck-Type Coupling of Vinylarenes with Alkyl Iodides
Haigen Xiong1,2, Yajun Li1, Bo Qian1
1Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis , Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences , 155 Yangqiao Road West , Fuzhou , Fujian 350002 , P. R. of China.
Abstract:
An iron(II)-catalyzed radical alkyl Heck-type reaction of alkyl iodides with vinylarenes under mild conditions has been reported. t-Butyl peroxybenzoate (TBPB) behaves simultaneously as a radical relay initiator, a precursor for the generation of alkyl radical from alkyl iodides, and an oxidant to recycle iron(II)/iron(III). Unactivated primary, secondary, and tertiary alkyl iodides are compatible with the reaction conditions. The mechanistic studies suggest that a radical-polar-crossover pathway might be involved in the catalytic cycle.
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