Site-Selective C-C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy Using Nickel Catalysis

Controlling the chemo- and regioselectivity of transition-metal-catalyzed C-C activation remains a great challenge. The transformations of benzocyclobutenones (BCBs) usually involve the cleavage of C1-C2 bond. In this work, an unprecedented highly selective cleavage of C1-C8 bond with the insertion of alkynes is achieved by using blocking strategy via Ni catalysis, providing an efficient method for synthesis of 1,8-disubstituted naphthalenes. Notably, the blocking group could be readily removed after the transformation.

Automated summary

In this study, an unprecedented highly selective cleavage of C1-C8 bond with the insertion of alkynes was achieved by using a blocking strategy via Ni catalysis. This provides an efficient method for the synthesis of 1,8-disubstituted naphthalenes, with the potential for easy removal of the blocking group after the transformation.