2009/07/27 by Kwame Frimpong, Joseph S. Wzorek, Claire M. Lawlor +2 · 1 citation
Chemistry · #Chemical synthesis and alkaloids #Cyclization and Aryne Chemistry #Synthetic Organic Chemistry Methods
paper · pdf · doi:10.1021/jo900763u
openalex publication_date 2009/07/27 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/22
Indium-promoted coupling reactions between propargyl aldehydes (1) and alpha-chloropropargylphenyl sulfide are reported. Although water has been shown to accelerate indium metal promoted reactions, the reverse pattern was observed in this series. Use of N-methylformamide (NMF), which has not previously been a solvent known for use in indium-promoted reactions, afforded an acceleration of these Barbier-style reactions compared to water. Indium-promoted reactions in this study also showed excellent regiocontrol and good stereocontrol, allowing for easy entry into the formation of epoxydiyne and enediyne skeletal structures. This paper also describes use of the Barbier Coupled product (2) as a new, and easy, entry into the formation of enediyne and epoxydiyne skeletal structures.