PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes: dual role of the Pt catalyst.
1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr(2)-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr(2) acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the enyne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.
Bajracharya
Gan B
GB
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Nakamura
Itaru
I
Yamamoto
Yoshinori
Y