One-pot two-step oxidative cleavage of 1,2-arylalkenes to aryl ketones instead of arylaldehydes in an aqueous medium: A complementary approach to ozonolysis

Naina Sharma, Abhishek Sharma, Rakesh Kumar, Amit Shard, Arun K. Sinha

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A new approach has been developed for a one-pot and selective oxidative cleavage of aryl- and 1,2-diarylalkenes leading to one-carbon shorter aryl ketones; thereby, providing a complementary approach to classical ozonolysis. The methodology was applicable to diverse aromatic and polyaromaticarylalkenes bearing electron-donating or -withdrawing groups on the aromatic ring. The protocol also provided a useful one-pot oxidative cleavage-condensation sequence, which could potentially have important applications in natural product total synthesis. A one-pot, two-step approach has been achieved for the oxidative cleavage of 1,2-disubstituted arylalkenes into the corresponding aryl ketones instead of arylaldehydes (see scheme; NIS = N-iodosuccinimide; CTAB = cetyltrimethylammonium bromide; PDC/TBHP = pyridinium dichromate/tert-butyl hydroperoxide). The methodology also led to a valuable one-pot oxidative cleavage-condensation reaction that has widespread utility in the total synthesis of natural products.

Original languageEnglish
Pages (from-to)6025-6032
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number31
DOIs
StatePublished - Nov 2010

Keywords

  • Alkenes
  • Cleavage reactions
  • Ketones
  • Microwave chemistry
  • Oxidation

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