Photocatalytic -Alkylation of H-Diaryl Sulfondiimines via Anti-Markovnikov Hydroamination with Styrenes.

Org Lett

Research Center for Chemical Biology and Omics Analysis, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Boulevard, Shenzhen, Guangdong 518055, P. R. China.

Published: December 2023

AI Article Synopsis

  • Sulfondiimines are an underexplored but interesting pharmacophore in drug discovery, similar in structure to sulfones and sulfoximines.
  • The study introduces a simple and mild photocatalytic method for anti-Markovnikov hydroamination of styrenes, enabling the creation of -alkylated sulfondiimines with various alkyl groups.
  • This method was crucial in synthesizing a sulfondiimine-related analogue of the well-known drug Vioxx.

Article Abstract

Sulfondiimines, which are isoelectronic with sulfones and sulfoximines, represent a neglected yet intriguing pharmacophore in the discovery program. Herein, we present a facile and mild photocatalytic anti-Markovnikov hydroamination of styrenes for the construction of -alkylated sulfondiimines with primary, secondary, and tertiary alkyl substituents. A sulfondiimine-derived analogue of the marketed drug Vioxx was synthesized using this method as the key step.

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Source
http://dx.doi.org/10.1021/acs.orglett.3c03608DOI Listing

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