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Palladium catalyzed Sonogashira reactions of organic tellurides

Posted on:2017-10-10Degree:M.SType:Thesis
University:Western Illinois UniversityCandidate:Siraswal, ParvinlalFull Text:PDF
GTID:2451390008952829Subject:Organic Chemistry
Abstract/Summary:
The Sonogashira reaction is a Pd-catalyzed cross-coupling reaction of terminal alkynes with aryl or alkenyl halides in the presence of a co-catalyst cuprous iodide and a strong base. Sonogashira coupling is the main pathway for the synthesis of aryl alkynes and conjugated enynes. It gained its importance because of its simplicity and mild reaction conditions.;In our research we developed a new optimized method to perform Sonogashira coupling reaction of diaryl tellurides, divinyl tellurides, and dialkynyl tellurides with terminal alkynes. The coupling reactions were performed using Pd(dppf)Cl2 as a catalyst, CuI as a co-catalyst in the presence of K 2CO3 in DMSO. The reactions were carried out at room temperature and completed within 2 h when phenyl acetylene was used as a terminal alkyne. For other alkynes, such as 1-hexyne and 1-octyne, an elevated temperature and longer reaction time were needed for the completion of the reactions. This process resulted in good yields of Sonogashira coupling products at mild reaction conditions.
Keywords/Search Tags:Reaction, Sonogashira, Coupling, Tellurides, Alkynes
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