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Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne
Synlett ( IF 1.7 ) Pub Date : 2020-08-21 , DOI: 10.1055/s-0040-1706417
Mitsuru Shindo 1 , Takayuki Iwata 1 , Tatsuro Yoshinaga 2
Affiliation  

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 α,α-dibromoester under microflow conditions was continuously added to the flow reaction with benzyne, which successfully synthesized triptycene in only one minute.

中文翻译:

通过Ynolate三环加成对苯炔的流动合成三苯甲基

使用炔醇酯与苄基的三重环加成实现了三苯乙烯的流动合成。使用硼酸盐型苯炔前体,在微流条件下有效抑制了由烷基锂加入到苯中引发的副反应,从而以比相应批次条件下获得的更高产率生产出三苯乙烯。此外,将α,α-二溴酯在微流条件下制备的炔诺酸酯连续加入到与苄的流动反应中,仅在一分钟内就成功合成了三苯乙烯。
更新日期:2020-08-21
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