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Triethylaluminum- or Triethylborane-Induced Free Radical Reaction of Alkyl Iodides and α,β-Unsaturated Compounds

2003; American Chemical Society; Volume: 68; Issue: 10 Linguagem: Inglês

10.1021/jo020681b

1520-6904

Jing-Yuan Liu, Yoeng-Jiunn Jang, Wen-Wei Lin, Ju‐Tsung Liu, Ching‐Fa Yao,

Vanadium and Halogenation Chemistry

A series of alpha,beta-unsaturated compounds, 1a-c, 9, 13, and 17, were used as reactants in free radical conjugate addition reactions with different radicals generated from alkyl iodides such as 3, 4, or 5 in the presence of triethylborane-oxygen in air or via the use of triethylaluminum-benzoyl peroxide as a free radical initiator. When the reactions were carried out using triethylborane-air, the products, in most cases, were clean and were easily purified. However, higher yields of the 1,4-adducts and less side reactions occurred when less reactive substrates were used as Michael acceptors in reactions with triethylaluminum-benzoyl peroxide and alkyl iodide under similar conditions. A mechanism for this is proposed in Scheme 1.