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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 2
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Synthetic Communications Reviews

Diorganyl tellurides as substrates in Sonogashira coupling reactions under mild conditions

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Pages 217-225 | Received 10 Sep 2019, Published online: 18 Nov 2019
 

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.

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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.

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