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用于可见光磺酰化反应的通用平台:由催化性三芳基胺EDA配合物实现

A General Platform for Visible Light Sulfonylation Reactions Enabled by Catalytic Triarylamine EDA Complexes.

作者信息

Lasso Juan D, Castillo-Pazos Durbis J, Salgado Jan Michael, Ruchlin Cory, Lefebvre Loric, Farajat Daliah, Perepichka Dmytro F, Li Chao-Jun

机构信息

Department of Chemistry, McGill University, Montreal, Quebec H3A 0B8, Canada.

FRQNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, Quebec H3A 0B8, Canada.

出版信息

J Am Chem Soc. 2024 Jan 31;146(4):2583-2592. doi: 10.1021/jacs.3c11225. Epub 2024 Jan 17.

Abstract

Catalytic electron donor-acceptor (EDA) complexes have recently emerged as a powerful and sustainable alternative to iridium- and ruthenium-based photoredox synthetic methods. Yet, these complexes remain underexplored and reliant on the use of meticulously designed acceptors that require previous installation. Herein, we report a novel EDA complex employing tris(4-methoxyphenyl) amine as a catalytic donor for the sulfonylation of alkenes using inexpensive and readily available sulfonyl chlorides. Applying this operationally simple, visible-light-mediated general platform, we report both the redox-neutral and net-reductive functionalization of more than 60 substrates, encompassing vinylic or allylic sulfonylation, hydrosulfonylation, and sulfamoylation of activated and unactivated alkenes and alkynes.

摘要

催化电子供体-受体(EDA)配合物最近已成为基于铱和钌的光氧化还原合成方法的一种强大且可持续的替代方法。然而,这些配合物仍未得到充分探索,并且依赖于使用精心设计的、需要预先安装的受体。在此,我们报道了一种新型的EDA配合物,它使用三(4-甲氧基苯基)胺作为催化供体,以廉价且易于获得的磺酰氯对烯烃进行磺酰化反应。应用这个操作简单、可见光介导的通用平台,我们报道了60多种底物的氧化还原中性和净还原官能团化反应,包括烯丙基或烯丙基磺酰化、氢磺酰化以及活化和未活化烯烃及炔烃的氨磺酰化反应。

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