Journal of Organic Chemistry 2002-07-26

Synthesis of [n]- and [n.n]cyclophanes by using Suzuki-Miyaura coupling.

Beverly B Smith, Darron E Hill, T Ashton Cropp, Rosa D Walsh, David Cartrette, Sherry Hipps, Amy M Shachter, William T Pennington, William R Kwochka

Index: J. Org. Chem. 67(15) , 5333-7, (2002)

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Abstract

Reaction of the bis-9-BBN adduct of several dienes with 1,3-dibromobenzene via Suzuki coupling leads to a series of [n]metacyclophanes ranging in size from 10 to 17 atom members. In each case, two carbon-carbon bonds are formed in one reaction vessel. However, when the bis-9-BBN adduct of 1,5-hexadiene is coupled with a variety of aryl dihalides, larger [n.n]cyclophanes were formed in preference to the [n]cyclophanes. Four carbon-carbon bonds are formed in this instance. Single-crystal X-ray analyses of these [n.n]cyclophanes reveal interestingly shaped molecules with large cavities.