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金/铜催化与铜/光氧化还原催化的融合: -丙炔酰胺制备烷基恶唑的方法。

Merging Gold/Copper Catalysis and Copper/Photoredox Catalysis: An Approach to Alkyl Oxazoles from -Propargylamides.

机构信息

Institute of Functional Organic Molecular Engineering, Henan International Joint Laboratory of Medicinal Plants Utilization, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.

School of Pharmacy, Henan University, Kaifeng 475004, P. R. China.

出版信息

J Org Chem. 2021 Dec 17;86(24):18247-18256. doi: 10.1021/acs.joc.1c02668. Epub 2021 Dec 6.

Abstract

Here, we report a mild and highly efficient approach to alkyl oxazoles through merging gold/copper catalysis and copper/photoredox catalysis. Various alkyl oxazoles are synthesized from -propargylamides with alkyl halides in good to excellent yields with wide functional-group compatibility under blue-light irradiation. Significantly, a copper catalyst plays a dual role in this transformation: as a powerful cocatalyst to accelerate protodeauration of vinyl gold intermediates and improve photoredox catalysis.

摘要

在这里,我们报告了一种温和且高效的方法来合成烷基恶唑,该方法融合了金/铜催化和铜/光氧化还原催化。在蓝光照射下,各种烷基卤化物与 -丙炔酰胺反应,以良好至优秀的收率合成了各种烷基恶唑,具有广泛的官能团兼容性。值得注意的是,铜催化剂在这一转变中发挥了双重作用:作为一种强大的助催化剂,加速了乙烯基金中间体的脱质子化,并提高了光氧化还原催化的效率。

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