Electrophilic cyanations. I. Synthesis of thiocyanato-heteroarenes and tosylheteroarenes from mercapto-heteroarenes using p-toluenesulfonyl cyanide

Article abstract of DOI:10.3987/COM-97-7740

Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).