Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne

被引：11

作者：

Iwata, Takayuki ^{[1
]}

Yoshinaga, Tatsuro ^{[2
]}

Shindo, Mitsuru ^{[1
]}

机构：

[1] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Kasuga, Fukuoka 8168580, Japan

来源：

SYNLETT | 2020年 / 31卷 / 19期

基金：

日本学术振兴会;

关键词：

triptycene; ynolate; benzyne; flow synthesis; cycloadditionborate; ALDER REACTION; GENERATION; ARYNES; DERIVATIVES; LITHIATION; IPTYCENES; CHEMISTRY; QUINONES; DESIGN;

D O I：

10.1055/s-0040-1706417

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Flow synthesis of triptycene was achieved using triple cycloaddition of ynolate to benzyne. Employing the borate-type benzyne precursor, side reactions triggered by the addition of alkyllithium to benzyne were efficiently suppressed under microflow conditions, thus producing triptycene with a higher yield than that obtained under the corresponding batch conditions. Furthermore, ynolate prepared from alpha,alpha-dibromoester under microflow conditions was continuously added to the flow reaction with benzyne, which successfully synthesized triptycene in only one minute.

引用

页码：1903 / 1906

页数：4

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