Pd-catalyzed orthogonal Knoevenagel/Perkin condensation-decarboxylation- heck/Suzuki sequences: Tandem transformations of benzaldehydes into hydroxy-functionalized antidiabetic stilbene-cinnamoyl hybrids and asymmetric distyrylbenzenes

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

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Tandem reactions that involve chemoselective Knoevenagel/Perkin condensation-decarboxylation-Heck/Suzuki coupling or Heck-aldol sequences have been achieved. This enabled the first concise and efficient synthesis of several important hydroxy-functionalized compound classes, such as stilbene-cinnamoyl hybrids (potent protein tyrosine phosphatase1B inhibitors), cinnamoyl-cinnamic acid hybrids, asymmetric distyrylbenzenes, and biarylstyrenes. Previously reported synthesis require multiple steps and protection/deprotection manipulations.

Original languageEnglish
Pages (from-to)10350-10356
Number of pages7
JournalChemistry - A European Journal
Volume17
Issue number37
DOIs
StatePublished - 5 Sep 2011

Keywords

  • Ci-C coupling
  • condensation
  • olefination
  • palladium
  • stilbenoids

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