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钯催化的砜亚胺与芳基磺酸盐的N-芳基化反应

Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates.

作者信息

Yang Qingjing, Choy Pui Ying, Zhao Qingyang, Leung Man Pan, Chan Hoi Shan, So Chau Ming, Wong Wing-Tak, Kwong Fuk Yee

机构信息

The Hong Kong Polytechnic University Shenzhen Research Institute (SZRI) , Shenzhen 518057 , P. R. China.

Department of Chemistry , The Chinese University of Hong Kong , Shatin , New Territories , Hong Kong.

出版信息

J Org Chem. 2018 Sep 21;83(18):11369-11376. doi: 10.1021/acs.joc.8b01599. Epub 2018 Aug 13.

Abstract

Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -Cl and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc)/MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.

摘要

成功实现了钯催化的亚磺酰亚胺与芳基卤化物(如 -Br、-I、-Cl 以及拟卤化物 -OTf 和 -ONf)之间的 C-N 键偶联反应。然而,芳基甲苯磺酸酯/甲磺酸酯的反应效果仍有待提高。在本报告中,描述了一种用芳基磺酸酯对亚磺酰亚胺进行的通用 N-芳基化反应。使用 Pd(OAc)/MeO-CM-phos 配合物,可以以良好至优异的产率(高达 99%)获得 N-芳基亚磺酰亚胺产物,且具有良好的常见官能团兼容性。除了芳烃部分外,烯基甲苯磺酸酯也被证明是成功的偶联伙伴。

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