Science of Synthesis

Pitaval, A.; Echavarren, A. M., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 1, 536.

The Stille coupling of aryl bromides and iodides with organostannanes using palladium(II) acetate and 1,4-diazabicyclo[2.2.2]octane (DABCO) as ligand proceeds with very high turnover numbers (‌Scheme 13‌).[‌189‌] 1,4-Diazabicyclo[2.2.2]octane also proves to be an excellent ligand for the palladium-catalyzed Suzuki–Miyaura cross-coupling reaction of aryl halides with arylboronic acids.[‌190‌–‌192‌] Under these conditions, high turnover numbers can be achieved (up to 950 000 for the reaction of iodobenzene with 4-chlorophenylboronic acid). Aryl chlorides can also be coupled by this method.

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References