Activation of CX (=Cl, Br) bond in aryl halides toward the palladium-catalyzed Heck reaction using 2,6-bis(diphenylphosphino)pyridine

The 2,6-bis(diphenylphosphino)pyridine/palladium catalytic system successfully catalyzes the Heck coupling reaction of less reactive aryl chlorides as well as aryl bromides with styrene to give the corresponding olefins in reasonable yields. TBAB (tetrabutylammoniumbromide) as an additive was found to be essential for these reactions. The results of Heck reaction exhibited a high selectivity (>99/1) favoring the trans product.

Graphical abstractThe 2,6-bis(diphenylphosphino)pyridine, (Ph2P)2py, has been used to the palladium-catalyzed Heck coupling reaction of less reactive aryl chlorides as well as aryl bromides.Figure optionsDownload full-size imageDownload high-quality image (104 K)Download as PowerPoint slideHighlights► Application of a 2,6-bis(diphenylphosphino)pyridine, in Pd-catalyzed Heck reaction. ► Aryl chlorides afforded good to excellent yield of coupling products. ► The results of Heck reaction exhibited a high selectivity (>99/1) favoring the trans product.