Triethylaluminum- or triethylborane-induced free radical reaction of alkyl iodides and α,β-unsaturated compounds

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

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Abstract

A series of α,β-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.

Original languageEnglish
Pages (from-to)4030-4038
Number of pages9
JournalJournal of Organic Chemistry
Volume68
Issue number10
Publication statusPublished - 2003 May 16

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ASJC Scopus subject areas

  • Organic Chemistry

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