Regioselective Synthesis of 1,4 & 1,5-Enynes through a Ca(II)- Catalyzed Cross-Dehydrative-Coupling of Styrenes and Propargyl alcohols

Srinivasarao Yaragorla, Ravikrishna Dada, Abhishek Pareek

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

A chemo and regioselective C(sp3) – C(sp2) and C(sp3) – C(sp3) bond formation through a Cross-Dehydrative-Coupling of styrenes and propargyl alcohols is described for the synthesis of 1,4 and 1,5-enynes. The first direct coupling of cyclic alkenes with oxindole derived propargylic alcohols is achieved for the synthesis of quaternary centered enynes under mild reaction conditions and demonstrated the gram scale synthesis. This approach meets the sustainable criterion of chemical synthesis due to its air-tolerance, atom economic (water is the only by-product), solvent free and use of less expensive and more abundant Ca(II) as the promoter.

Original languageEnglish (US)
Pages (from-to)495-499
Number of pages5
JournalChemistrySelect
Volume3
Issue number2
DOIs
StatePublished - Jan 17 2018
Externally publishedYes

Bibliographical note

Funding Information:
RD and AP are thankful to School of Chemistry, UGC-Networking Center, University of Hyderabad for the facilities.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Calcium catalysis
  • Dehydrative cross coupling
  • Enynes
  • Oxindoles
  • Propargyl alcohols

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