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Rh(III)-Catalyzed Tandem Acylmethylation/Nitroso Migration/Cyclization of N-Nitrosoanilines with Sulfoxonium Ylides in One Pot: Approach to 3-Nitrosoindoles

Yingtao Wu, Chao Pi, Xiuling Cui* and Yangjie Wu*

*Green Catalysis Center and College of Chemistry, Zhengzhou University, No. 75 Daxue Road, Zhengzhou, Henan 450052, P. R. China, Email: cuixlzzu.edu.cn, wyjzzu.edu.cn

Y. Wu, C. Pi, X. Cui, Y. Wu, Org. Lett., 2020, 22, 331-334.

DOI: 10.1021/acs.orglett.9b03768 (free Supporting Information)


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Abstract

Rh(III)-catalyzed acylmethylation and trifluoroacetic acid (TFA)-mediated nitroso transfer/cyclization cascade reaction provides 3-nitrosoindoles starting from easily available N-nitrosoanilines and sulfoxonium ylides. This process is scalable and avoids external oxidation. Moreover, further chemical transformations of the 3-nitrosoindoles enhance their synthetic value.

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ID: J54-Y2020