Synthesis of [n]- and [n.n]cyclophanes by using Suzuki-Miyaura coupling.
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.
Smith
Beverly B
BB
Department of Chemistry and Physics, Western Carolina University, Cullowhee, North Carolina 28723, USA.
Hill
Darron E
DE
Cropp
T Ashton
TA
Walsh
Rosa D
RD
Cartrette
David
D
Hipps
Sherry
S
Shachter
Amy M
AM
Pennington
William T
WT
Kwochka
William R
WR