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

Research output: Contribution to journalArticle

32 Citations (Scopus)

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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Unsaturated compounds
Free radical reactions
Benzoyl Peroxide
Iodides
Free Radicals
Air
Addition reactions
Oxygen
Substrates
triethylborane
triethylaluminum

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Triethylaluminum- or triethylborane-induced free radical reaction of alkyl iodides and α,β-unsaturated compounds. / Liu, Jing Yuan; Jang, Yoeng Jiunn; Lin, Wen-Wei; Liu, Ju Tsung; Yao, Ching-Fa.

In: Journal of Organic Chemistry, Vol. 68, No. 10, 16.05.2003, p. 4030-4038.

Research output: Contribution to journalArticle

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