Rc. Larock et al., PALLADIUM-CATALYZED INTERMOLECULAR ARYLATION OF FUNCTIONALLY-SUBSTITUTED CYCLOALKENES BY ARYL IODIDES, Tetrahedron, 50(2), 1994, pp. 305-321
The palladium-catalyzed, intermolecular arylation of functionally-subs
tituted cycloalkenes by aryl iodides affords a new synthetic route to
a variety of arylated cyclic derivatives. The arylation of 2-cyclopent
en-1-ol and 2-cyclo-hexen-1-ol provides modest yields of the correspon
ding 3-arylcycloalkanones, while 2-methyl-2-cyclopenten-1-ol affords a
mixture of singly and doubly arylated cyclopentanone products. 1-Acet
oxycyclopentene undergoes arylation to produce the corresponding allyl
ic aryl substitution product opening up a new route far the alpha-aryl
ation of cycloalkanones. Cyclic allylic ethers undergo arylation at bo
th ends of the C-C double bond to generate mixtures of singly arylated
vinylic ethers. 1-Cyanocyclopentene reacts with aryl iodides under pa
lladium catalysis to produce 1-cyano-5-arylcyclopentenes in high yield
. 2-Methyl-2-cycloalken-1-ones afford modest yields of doubly arylated
2-cycloalken-1-ones in a single step.