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光照诱导的钌催化氮宾转移反应:一种构建 N-酰基亚磺酰胺和亚磺酰亚胺的光化学方法。

Light-induced ruthenium-catalyzed nitrene transfer reactions: a photochemical approach towards N-acyl sulfimides and sulfoximines.

机构信息

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany) http://bolm.oc.rwth-aachen.de/

出版信息

Angew Chem Int Ed Engl. 2014 May 26;53(22):5639-42. doi: 10.1002/anie.201310790. Epub 2014 Apr 9.

Abstract

1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported.

摘要

1,4,2-二恶唑-5-酮是一种五元杂环化合物,已知在热或光化学条件下脱羧,从而生成 N-酰基氮宾。本文描述了一种光诱导的钌催化 N-酰基氮宾转移到硫化物和亚砜的方法,通过 1,4,2-二恶唑-5-酮在室温下脱羧,从而在温和的反应条件下直接得到 N-酰基亚磺酰胺和亚磺酰胺。此外,还报道了一种由单个钌配合物催化的一锅法硫代亚胺化/氧化反应序列。

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