“…With 1.0 equivalents of NIS, the reaction generated 81% yield of 1-iodoalkyne 3aa (entry 12). However, when higher or lower amount of Al 2 O 3 was used, low yields of the desired product were observed (entry [13][14][15]. Finally, the best conditions to obtain the 1-iodoalkyne 3aa were treatment of 1aa with 1.1 equivalents of NIS, 1.3 equivalents of neutral g-Al 2 O 3 and 4 A MS in CH 3 CN at 80 C for 1 h. With the optimized conditions in hand, we also studied the halogenation of phenyl acetylene 1aa and used various halogenated reagents, including N-bromosuccinimide, 1,3-dibromo-5,5dimethylhydantoin, pyridinium tribromide and N-chlorosuccinimide.…”