Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation

Wey Chyng Jeng, Po Chung Chien, Sandip Sambhaji Vagh, Athukuri Edukondalu, Wenwei Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides that is catalyzed by organophosphanes in the presence of base. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under mild, metalfree conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/rearrangement sequence. Mechanistic investigations revealed that C-O bond cleavage on a possible betaine intermediate is the key step for the installation of the keto-functionality at the β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by a scale-up reaction and synthetic transformations of the products.

Original languageEnglish
Pages (from-to)4409-4418
Number of pages10
JournalSynthesis (Germany)
Volume53
Issue number23
DOIs
Publication statusPublished - 2021 Dec 1

Keywords

  • functionalized 2-ylideneoxindoles
  • indolin-3-ones
  • phospha-Michael addition
  • phosphine catalysis
  • β-acylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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