Arylations with the Sonogashira-Hagihara Reaction

For a very recent 2011 review on this subject, the reader is encouraged to consult the review of Chinchilla and Ndjera [107a]. 

Traditiontdly, Pd or Pd/Cu salts have been used but over the years, this reaction can be stretched to include other mettils such as iron, ruthenium, cobalt, nickel, silver indium, and gold [107b]. In the case of gold, there was some controversy, and in certain quarters, there was talk of contamination of the gold cattdyst with ptJladium (see below). 

PdCl2(PPh3)2(2 mol%), Cul, nBu4NI, Et2NH, MeCN, rt R = + Ar-N2BF4 -------------------------------  

In 2011, Lipshutz s team reported the successful application of the amphiphile TPGS-750-M for the realization of Sonogashira-Hagihara coupling reactions (as well as Heck-Mizoroki, Suzuki-Miyaura, Buchwald-Hartwig, Negishi-like couplings, C-H activation reactions, and so on 

The Suzuki-Miyaura reaction is one of the most prominent and useful coupling reactions over the last few years, its usefulness has been reported in several papers and patents, and in this section, a cross-section of these reports is given. 

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