Functionalization via [6,6] Detailed mechanistic understanding of the often complex copper mediated C-H activation reactions remains limited as cupracyclic intermediates are relatively unstable and only a handful of stable organocuprates have been reported to date. Our attempts at direct investigation of the potential imine coordinated organocuprate intermediate were unsuccessful. Despite these challenges, we wanted to gain insight into the role and performance of the catalytic transient directing groups and underlying mechanism of the C-H functionalization. Therefore, to interrogate the reaction mechanism kinetic and deuteration experiments were undertaken.