gem-Difunctionalization of α-diazoarylketones with diaryldiselenides and N-halosuccinimides: facile synthesis of α-halo-α-arylseleno ketones

Abstract: An efficient synthesis of α-halo-α-arylseleno ketones has been developed via gem-difunctionalization of α-diazoarylketones with diaryldiselenides and N-halosuccinimides. With this multicomponent approach, a series of α-halo-α-arylseleno ketones were accessed in excellent yields and chemoselectivities under mild conditions. This transformation is proposed to proceed via the key intermediate arylselenenyl halide that generated from diaryldiselenides/N-halosuccinimides, followed by addition with α-diazoarylketones to give the desired gem-difunctionalization products. Graphic Abstract: [Figure not available: see fulltext.]