Synthesis of a selenoformamide bearing both a hydroxy group and a bulky aryl substituent

Abstract Despite considerable research efforts devoted to the applications of selenoamides, derivatives bearing complex functional groups, such as bulky and/or convertible substituents, remain limited so far, probably due to the instability of the selenoamide moiety under several reaction conditions. Herein, we report the synthesis of a selenoformamide possessing both a free hydroxy group and a bulky aryl substituent, achieved via effective N-formylation using acetic formic anhydride and subsequent selenocarbonylation with LiAlHSeH of a sterically encapsulated position. The structure of the selenoamide was established by a single-crystal X-ray diffraction analysis. Although chemoselective transformation of the hydroxy group was found to be challenging, these insights provide a useful platform for further development of selenocarbonyl chemistry.