Diorganyl tellurides as substrates in Sonogashira coupling reactions under mild conditions

Abstract

A new method of Sonogashira coupling reactions between diorganyl tellurides and terminal alkynes is reported. The coupling reactions are performed using Pd(dppf)Cl₂ as a catalyst, CuI as a co-catalyst in the presence of K₂CO₃ in DMSO. The reactions are carried out at room temperature and completed within 2 h when phenyl acetylene is used as a terminal alkyne. For aliphatic terminal alkynes, such as 1-hexyne and 1-octyne, an elevated temperature and longer reaction time are needed for the completion of the reactions. This process results in good yields of Sonogashira coupling products which is applicable for diaryl, divinyl and dialkynyl tellurides but not applicable for dialkyl tellurides.

Graphical Abstract

Keywords:

• Symmetrical diorganyl telluride
• Sonogarshira coupling
• terminal alkynes
• palladium catalyst

Additional information

Funding

The authors are grateful to NSF MRI award (Acquisition of a 400-MHz NMR Spectrometer to Support Faculty-Student Research and Training at WIU and Partner Institutions), College of Arts and Science at WIU for financial support.