Oxy- and aminoselenation of alkenes utilizing an isolable selenenyl iodide

Application of an isolable selenenyl iodide BpqSeI (Bpq denotes 5',5'''-bis(2,6-diisopropylphenyl)-2,6,2'''',6''''-tetra-isopropyl-1,1':3',1'':3'',1''':3''',1''''-quinquephenyl-2''-yl) to selenofunctionalization of alkenes with external oxygen or nitrogen nucleophiles was investigated. In the presence of N-iodosuccinimide as an additive, alcohols, a carboxylic acid, or aromatic amines were smoothly introduced to alkenes to give the corresponding β-oxy or β-amino selenides in moderate to high yields.