Palladium-Catalyzed Suzuki Cross-Coupling of 2-Haloselenophenes: Synthesis of 2-Arylselenophenes, 2,5-Diarylselenophenes, and 2-Arylselenophenyl Ketones

Abstract

We present herein our results on the Suzuki coupling reaction of 2-haloselenophenes with boronic acids catalyzed by palladium salt and describe a new route established to prepare 2-arylselenophenes and 2,5-diarylselenophenes in good yields. The reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron-donating, and neutral substituents, in the presence of Pd(OAc)2, K2CO3/H2O in DME. In addition, by this protocol unsymmetrical aryl ketones were also obtained from 2-iodoselenophene and boronic acids via a carbonylative process.