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Palladium-Catalyzed Direct C-H Functionalization of Indoles with the Insertion of Sulfur Dioxide: Synthesis of 2-Sulfonated Indoles. 2017

Tong Liu, and Wei Zhou, and Jie Wu
Department of Chemistry, Fudan University , 220 Handan Road, Shanghai 200433, China.

A palladium-catalyzed direct C-H bond sulfonylation of indoles with the insertion of sulfur dioxide is achieved through a three-component reaction of 1-(pyridin-2-yl)indoles, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions. Diverse 2-sulfonated indoles are generated by using 10 mol % of palladium(II) bromide as the catalyst at room temperature. This synthetic approach is efficient by merging palladium catalysis and insertion of sulfur dioxide via a radical process. 2-Pyrimidinyl can be used as the directing group well as for the C-H bond sulfonylation. Additionally, the directing group can be easily removed.

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