TY - JOUR
T1 - Gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes
T2 - Intramolecular capture of the vinyl-au intermediate by the silicon electrophile
AU - Nakamura, Itaru
AU - Sato, Takuma
AU - Terada, Masahiro
AU - Yamamoto, Yoshinori
PY - 2007/9/27
Y1 - 2007/9/27
N2 - The gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes 1 produced the corresponding 3-silylbenzo[b]thiophenes 2 in good to excellent yields. For example, the reaction of [2-(1-pentynyl)phenylthio] triisopropylsilane 1a, [2-(p-anisylethynyl)phenylthio]triisopropylsilane 1e, and [2-(phenylethynyl)phenylthio]triisopropylsilane 1g in the presence of 2 mol % of AuCl in toluene at 45°C gave 2a, 2e, and 2g in 98, 99, and 97% yields, respectively. This reaction proceeds through intramolecular capture of the vinyl-Au intermediate by the silicon electrophile, so-called silyldemetalation.
AB - The gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes 1 produced the corresponding 3-silylbenzo[b]thiophenes 2 in good to excellent yields. For example, the reaction of [2-(1-pentynyl)phenylthio] triisopropylsilane 1a, [2-(p-anisylethynyl)phenylthio]triisopropylsilane 1e, and [2-(phenylethynyl)phenylthio]triisopropylsilane 1g in the presence of 2 mol % of AuCl in toluene at 45°C gave 2a, 2e, and 2g in 98, 99, and 97% yields, respectively. This reaction proceeds through intramolecular capture of the vinyl-Au intermediate by the silicon electrophile, so-called silyldemetalation.
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U2 - 10.1021/ol701951n
DO - 10.1021/ol701951n
M3 - Article
AN - SCOPUS:35048879619
SN - 1523-7060
VL - 9
SP - 4081
EP - 4083
JO - Organic Letters
JF - Organic Letters
IS - 20
ER -