title: Grignard reagents: alkoxide-directed iodine-magnesium exchange at sp3 centers.
abstract: Sequential addition of i-PrMgCl and BuLi to sp3 hybridized iodoalcohols triggers a facile iodine-metal exchange. Intercepting the resulting cyclic Grignard reagents with a slight excess of an electrophile leads to a diverse range of substituted alcohols. The iodine-magnesium exchange strategy is effective with 3-carbon iodoalcohols bearing alkyl substitutents on the carbinol or adjacent carbons and with the chain-extended homolog 4-iodobutan-1-ol.
authors.affiliation: Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu
authors.forename: Fraser F
authors.initials: FF
authors.lastname: Fleming
authors.forename: Subrahmanyam
authors.initials: S
authors.lastname: Gudipati
authors.forename: Viet Anh
authors.initials: VA
authors.lastname: Vu
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Mycka
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel