Grignard reagents: alkoxide-directed iodine-magnesium exchange at sp3 centers

Org Lett. 2007 Oct 25;9(22):4507-9. doi: 10.1021/ol701947y. Epub 2007 Oct 5.

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.