TY - JOUR
T1 - PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes
T2 - Dual role of the Pt catalyst
AU - Bajracharya, Gan B.
AU - Nakamura, Itaru
AU - Yamamoto, Yoshinori
PY - 2005/2/4
Y1 - 2005/2/4
N2 - (Chemical Equation Presented) 1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-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 PtBr2 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.
AB - (Chemical Equation Presented) 1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-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 PtBr2 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.
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U2 - 10.1021/jo048273q
DO - 10.1021/jo048273q
M3 - Article
C2 - 15675846
AN - SCOPUS:13244277647
VL - 70
SP - 892
EP - 897
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 3
ER -