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光诱导有氧碘芳烃催化N-氧代酰胺向N-稠合螺内酰胺的螺环化反应*

Photoinduced Aerobic Iodoarene-Catalyzed Spirocyclization of N-Oxy-amides to N-Fused Spirolactams*.

作者信息

Habert Loïc, Cariou Kevin

机构信息

Institut de Chimie des Substances Naturelles, LabEx LERMIT, UPR 2301, Université Paris-Saclay, CNRS, 1, avenue de la Terrasse, 91198, Gif-sur-Yvette, France.

Institute of Chemistry for Life and Health Sciences, Laboratory for Inorganic Chemical Biology, Chimie ParisTech, PSL University, CNRS, 11, rue Pierre et Marie Curie, 75005, Paris, France.

出版信息

Angew Chem Int Ed Engl. 2021 Jan 4;60(1):171-175. doi: 10.1002/anie.202009175. Epub 2020 Oct 26.

Abstract

Iodoarene catalysis is a powerful methodology that usually requires an excess of oxidant, or of redox mediator if the terminal oxidant is dioxygen, to generate the key hypervalent iodine intermediate to proceed efficiently. We report that, using the spiro-cyclization of amides as a benchmark reaction, aerobic iodoarene catalysis can be enabled by relying on a pyrylium photocatalyst under blue light irradiation. This unprecedented dual organocatalytic system allows the use of low catalytic loading of both catalysts under very mild operating conditions.

摘要

碘芳烃催化是一种强大的方法,通常需要过量的氧化剂,或者如果终端氧化剂是氧气,则需要过量的氧化还原介质,以生成关键的高价碘中间体,从而有效地进行反应。我们报道,以酰胺的螺环化反应作为基准反应,在蓝光照射下,依靠一种吡喃鎓光催化剂可以实现有氧碘芳烃催化。这种前所未有的双有机催化体系允许在非常温和的操作条件下使用低催化负载量的两种催化剂。

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