4-Benzylpiperidine (I) was alkylated with butynyl tosylate (II) to afford the N-butynyl piperidine (III). Subsequent coupling of (III) with 4-iodophenol (IV) in the presence of Pd(PPh3)4 in pyrrolidine produced the corresponding butynyl phenol.
4-Benzylpiperidine (I) was alkylated with propargyl tosylate (II) to afford the N-propynyl piperidine (III). Subsequent coupling of (III) with 4-iodophenol (IV) in the presence of Pd(PPh3)4 in pyrrolidine produced the corresponding propynyl phenol.