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Brønsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2022-11-02 , DOI: 10.1002/adsc.202200977
Cheng-Chun Chen, Tzu-Hsuan Kuan, Wen-Wei Yuan, Shih-En Chen, Jui-Chen Fu, Yang-Xun Chen, Hui-Hsu Gavin Tsai, Duen-Ren Hou

Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1-naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by 1H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate.

中文翻译:

Brønsted 酸促进邻炔基苯甲醛和炔烃的苯并环化,以及炔丙醇的积极作用

报道了溴三甲基硅烷促进炔基苯甲醛和炔烃的苯并环化以产生 1-萘基芳基酮。反应条件温和,不含金属,不需要对基材进行预处理/保护。我们发现,与其他炔烃相比,芳基炔丙醇是该反应非常有效的底物。反应范围研究、 1 H NMR监测反应进程和理论计算表明,异苯并吡啶离子是关键的反应中间体。
更新日期:2022-11-02
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