TMSOTf-Promoted Intermolecular Cascade Reaction of Aromatic Diazo Ketones with Olefins: Selective Synthesis of 3-Arylethylideneoxindoles

Madhu Babu Tatina, Wang Xinzhu, Mardi Santoso, Ziad Moussa, Zaher M.A. Judeh

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A simple trimethylsilyl trifluoromethanesulfonate (TMSOTf)-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins has been developed. This method directly gave 3-phenylethylideneoxindoles from 3-diazooxindoles and styrenes with exclusive regioselectivity, chemoselectivity, and E-stereoselectivity. The key to the success of the reaction and higher yields is the elegant use of TMSOTf, which gradually released the active triflic acid promoter in situ. The reaction tolerates a wide substrate scope of 3-diazooxindoles and styrenes with electron-donating and electron-withdrawing groups and works well on the gram scale.

Original languageEnglish
Pages (from-to)9129-9138
Number of pages10
JournalJournal of Organic Chemistry
Volume85
Issue number14
DOIs
Publication statusPublished - Jul 17 2020

ASJC Scopus subject areas

  • Organic Chemistry

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