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Catalytic Arene meta-C–H Functionalization Exploiting a Quinoline-Based Template

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posted on 17.03.2017, 00:00 by Uttam Dutta, Atanu Modak, Bangaru Bhaskararao, Milan Bera, Sukdev Bag, Anirban Mondal, David W. Lupton, Raghavan B. Sunoj, Debabrata Maiti
Strong σ-coordination by a heteroatom containing directing group (DG) is one of the effective strategies for performing site-selective C–H functionalization. Despite tremendous progress in directed ortho-C–H functionalization, selective meta-C–H functionalization using strong σ-coordination remains extremely challenging. Herein, we introduce the 8-nitroquinoline-based DG to ensure the formation of a stable palladacycle which enables selective meta-alkenylation and acetoxylation of arenes. Kinetic experiments, ESI-MS, NMR, and DFT studies provided important information regarding the mechanism of the reaction. The scalability as well as diversification of the products have been examined and are expected to be beneficial in pharmaceutical and material sciences.