Site‐Selective C–C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy Using Nickel Catalysis
Jing‐Hong Guo, Yu Liu, Xin‐Cheng Lin, Tian‐Mu Tang, Bi‐Qin Wang, Ping Hu, Ke‐Qing Zhao, Feijie Song, Zhang‐Jie Shi
Abstract
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.
Topics & Concepts
RegioselectivityCleavage (geology)CatalysisChemistryBond cleavageBlocking (statistics)NickelCombinatorial chemistryStereochemistryOrganic chemistryMaterials scienceComputer scienceComputer networkFracture (geology)Composite materialCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsAsymmetric Hydrogenation and Catalysis