Science of Synthesis

Griesbeck, A. G.; Soldevilla, A., Science of Synthesis, (2008) 43, 361.

In Sonogashira-type reactions, iodoarenes are most frequently used as the coupling partners for the alkynes. Using less-reactive bromo- and chloroarenes is an attractive option, as they are less expensive and more widely available than the iodides. Some Sonogashira protocols describing successful couplings using these substrates have been reported. These rely on the use of electron-rich palladium complexes, containing carbene ligands,[‌23‌,‌67‌] specially designed tetrapodal phosphine ligands,[‌68‌] or bulky phosphine ligands.[‌69‌] (Some other examples exist which do not require a copper(I) cocatalyst; see Section ‌43.6.1.3.5‌.)

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