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.