A Novel Method for the Synthesis of Haloisoquinolines Involving an Electrophile-exchange Process

A synthesis of haloisoquinolines through electrophilic cyclisation involving an electrophilic-exchange process has been developed. A variety of 2-alkynyl benzyl azides are cyclised in the presence of KX (X = I, Br, Cl) and electrophilic fluoride reagents, to afford the corresponding haloisoquinolines in moderate to good yields. Reagents for electrophilic halogenation have been generated from their inorganic salts (M + X - ) by oxidation with a Selectfluor reagent and reacted in situ with the substrates.