Nickel-catalyzed one-pot synthesis of biaryls from phenols and arylboronic acids via C–O activation using TCT reagent

• Nickel-catalyzed cross-coupling reactions of phenol derivatives with arylboronic acids.
• In situ activation of phenols using TCT for utilization in C–C coupling reactions.
• TCT as a cheap, readily available reagent for C–O bond activation of phenolic compounds.
• Direct synthesis of biaryls from phenols using TCT as C–O bond activator.

In this study, the direct Nickel-catalyzed Suzuki–Miyaura coupling reaction of phenols and arylboronic acids via C–O bond activation using 2,4,6-trichloro-1,3,5-triazine (TCT) is described. Initially, phenols were reacted with TCT to give the corresponding 2,4,6-triaryloxy-1,3,5-triazine (TAT) products. Subsequently, arylboronic acid, base and Ni-catalyst were added to the generated aryl C–O electrophile to obtain the final biaryl product. This study represents a simple and direct method for the synthesis of biaryls from phenolic compounds using sub-stoichiometric amounts of TCT as a cheap and readily available C–O activating reagent.

An efficient method is introduced for one-pot synthesis of biaryls from phenols and arylboronic acids using activation of phenolic C–O bond by TCT reagent.Figure optionsDownload as PowerPoint slide