Site-Selective Iodine−Magnesium Exchange Reaction of 1,4-Diiodo-1,3-Alkadienes by an Organomagnesium Ate Complex, and Its Application to Synthesis of Polysubstituted Styrenes and Phenols

When 1,4-diiodo-1,3-alkadienes were treated with i-PrBu2MgLi, highly site-selective iodine−magnesium exchange reaction took place to afford, after the reaction with electrophiles, a variety of 1-iodo-1,3-alkadiene derivatives. Synthetic utility of the reaction was demonstrated by an efficient prepar...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 125; no. 23; pp. 6884 - 6885
Main Authors Fukuhara, Kohki, Takayama, Yuuki, Sato, Fumie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.06.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Organic chemistry
Physical Sciences
Science & Technology
HALOGEN
ALKYNES
EFFICIENT
DERIVATIVES
One pot reaction
Regioselectivity
Styrene derivatives
Benzenic compound
Magnesium Organic compounds
Exchange reaction
Dienic compound
Experimental study
Iodocarbon
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Summary:When 1,4-diiodo-1,3-alkadienes were treated with i-PrBu2MgLi, highly site-selective iodine−magnesium exchange reaction took place to afford, after the reaction with electrophiles, a variety of 1-iodo-1,3-alkadiene derivatives. Synthetic utility of the reaction was demonstrated by an efficient preparation of polysubstituted styrenes and phenols.
Bibliography:istex:0F6586FB9BC973350E76D13C55624DC2D2D1653D
ark:/67375/TPS-WC5MDCPQ-S
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0353513