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连续流动条件下紫外光介导的苯乙烯硼环丙烷化反应

Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions.

作者信息

Sayes Morgane, Benoit Guillaume, Charette André B

机构信息

Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128 Station Downtown, Montreal, Quebec, H3C 3J7, Canada.

出版信息

Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13514-13518. doi: 10.1002/anie.201807347. Epub 2018 Sep 12.

Abstract

Herein, we report a user-friendly and metal-free UV-A light mediated borocyclopropanation of styrenes using continuous flow technology. A broad range of styrene derivatives can be cyclopropanated in good yields within 1 h residence time to produce highly valuable cyclopropylboronate esters with modest to good diastereoselectivities. The reaction is also applicable to α-substituted styrenes. Mechanistic studies support a photoredox process during which xanthone, a well-known organic photosensitizer, can easily reach a photoexcited state that is available for both an oxidative and a reductive quenching.

摘要

在此,我们报道了一种使用连续流技术,以用户友好且无金属的方式通过紫外-A光介导的苯乙烯硼环丙烷化反应。在1小时的停留时间内,多种苯乙烯衍生物可以以良好的产率进行环丙烷化反应,生成具有适度至良好非对映选择性的高价值环丙基硼酸酯。该反应也适用于α-取代的苯乙烯。机理研究支持了一种光氧化还原过程,在此过程中,一种著名的有机光敏剂呫吨酮可以很容易地达到光激发态,该光激发态可用于氧化猝灭和还原猝灭。

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