Aluminum Chloride Mediated Alkynylation of Boron Subphthalocyanine Chloride Using Trimethylsilyl-Capped Acetylenes

A mild and versatile procedure is presented for functionalization of boron chloride subphthalocyanine at the axial boron position with trimethylsilyl-protected alkyne nucleophiles in the presence of aluminum chloride. The method allows a large variety of substituents on the alkyne units, including electron-donating/withdrawing aryl groups, silyl-protected alkynyl groups, as well as ferrocenyl and azulenyl groups. In addition, ferrocene itself reacts smoothly under these conditions allowing for directly anchoring it to the boron of the subphthalocyanine.