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Synthesis of [n]- and [n.n]cyclophanes by using Suzuki-Miyaura coupling
Beverly B Smith1, Darron E Hill, T Ashton Cropp
1Department of Chemistry and Physics, Western Carolina University, Cullowhee, North Carolina 28723, USA.
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.
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