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

Kohki Fukuhara; Yuuki Takayama; Fumie Sato

doi:10.1021/ja0353513

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

J Am Chem Soc. 2003 Jun 11;125(23):6884-5. doi: 10.1021/ja0353513.

Authors

Kohki Fukuhara¹, Yuuki Takayama, Fumie Sato

Affiliation

¹ Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.

PMID: 12783538
DOI: 10.1021/ja0353513

Abstract

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.