SYNTHESIS OF BIS(BENZO[b]THIOPHENYL)METHANES BY GOLD-CATALYZED DOUBLE CARBOTHIOLATION

被引：7

作者：

Nakamura, Itaru ^{[1
,2
]}

Okamoto, Masashi ^{[2
]}

Sato, Takuma ^{[2
]}

Terada, Masahiro ^{[2
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

HETEROCYCLES | 2010年 / 82卷 / 01期

关键词：

Gold Catalyst; Cyclization; Benzothiophene; Carbothiolation; Alkyne; FIELD-EFFECT TRANSISTORS; CONTAINING AZOMETHINE YLIDES; ORGANIC TRANSFORMATIONS; PLATINUM; ALKYNES; CYCLOISOMERIZATION; DERIVATIVES; CYCLIZATION; SULFIDES; HETEROARENES;

D O I：

10.3987/COM-10-S(E)44

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed double cyclization of bis(2-alkynylphenylthio)acetals (1) produced bis(benzo[b]thiophen-3-yl)methanes (2) in good to excellent yields with high catalyst turnover number. For example, the reaction of (phenylmethylene)bis((2-(phenylethynyl)phenyl)sulfane) (1b) in the presence of 1 mol% of AuCl in toluene at 25 degrees C for 1 hour gave 3,3'-(phenylmethylene)bis(2-phenylbenzo[b]thiophene) (2b) in 97% isolated yield. The present reaction proceeded through two successive intramolecular carbon-sulfur bond addition reactions, or the so-called carbothiolation.

引用

页码：689 / 697

页数：9

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