Stepwise delivery of two methoxy groups of arylaldehyde acetals across the phenyl ring. Vacant site-controlled palladium catalysis.
A new catalytic cyclization of o-alkynylbenzaldehyde acetals 1 to the functionalized indenes 2 was found to be strictly controlled by the number of triphenylphosphine ligands on the Pd catalyst. Only complexes with three available coordination sites on Pd catalyze this reaction. Mechanistic study suggests that pi-coordination of Pd to the benzene ring is a key step controlled by the number of vacant coordination sites.
Nakamura
Itaru
I
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. itaru-n@mail.tains.tohoku.ac.jp
Mizushima
Yuya
Y
Gridnev
Ilya D
ID
Yamamoto
Yoshinori
Y