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光催化自由基 - 去芳构化环化反应:构建螺[4.5]癸 - 1,7,9 - 三烯 - 6 - 酮类化合物

Photocatalytic Radical -Dearomative Cyclization: Access to Spiro[4.5]deca-1,7,9-trien-6-ones.

作者信息

Dong Wuheng, Yuan Yao, Liang Caiyun, Wu Feng, Zhang Siyuan, Xie Xiaomin, Zhang Zhaoguo

机构信息

Medicine Center, Guangxi University of Science and Technology, Liuzhou, Guangxi 545006, China.

Guangxi Key Laboratory of Green Processing of Sugar Resources, Liuzhou, Guangxi 545006, China.

出版信息

J Org Chem. 2021 Mar 5;86(5):3697-3705. doi: 10.1021/acs.joc.0c02477. Epub 2021 Jan 19.

Abstract

A highly efficient -dearomative cyclization reaction between alkynes and 2-bromo-2-(2-methoxybenzyl)malonate via visible light-induced photoredox catalysis has been reported. In the presence of 1 mol % -Ir(ppy), a variety of spiro[4.5]deca-1,7,9-trien-6-ones were obtained in moderate to excellent yields under mild conditions. Under the optimized reaction conditions, a sample reaction of 3 mmol scale proceeded smoothly to give the desired products in 84% yield with a low catalyst loading of 0.1 mol %.

摘要

据报道,通过可见光诱导的光氧化还原催化,炔烃与2-溴-2-(2-甲氧基苄基)丙二酸酯之间发生了高效的脱芳构化环化反应。在1 mol%的-Ir(ppy)存在下,在温和条件下以中等至优异的产率得到了多种螺[4.5]癸-1,7,9-三烯-6-酮。在优化的反应条件下,3 mmol规模的样品反应顺利进行,以84%的产率得到所需产物,催化剂负载量低至0.1 mol%。

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