Reactivity of p-Toluenesulfonylmethyl Isocyanide: Iron-Involved C-H Tosylmethylation of Imidazopyridines in Nontoxic Media.

J Org Chem

College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University, No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.

Published: September 2016

A novel iron-involved tosylmethylation of imidazo[1,2-α]pyridines with p-toluenesulfonylmethyl isocyanide in a solvent mixture of H2O and PEG400 under an Ar atmosphere has been developed. This protocol provides a facile synthetic route for the functionalization of the imidazo[1,2-α]pyridine scaffold with broad substrate compatibility, which is less expensive and environmentally friendly. The current methodology could further enable regioselective C-H tosylmethylation of indole at the C3 position. Also, p-toluenesulfonylmethyl isocyanide was utilized as the tosylmethylating reagent for the first time.

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http://dx.doi.org/10.1021/acs.joc.6b01552DOI Listing

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