Catalytic arene meta-C–H functionalization exploiting a quinoline-based template

Dutta, Uttam ; Modak, Atanu ; Bhaskararao, Bangaru ; Bera, Milan ; Bag, Sukdev ; Mondal, Anirban ; Lupton, David W. ; Sunoj, Raghavan B. ; Maiti, Debabrata (2017) Catalytic arene meta-C–H functionalization exploiting a quinoline-based template ACS Catalysis, 7 (5). pp. 3162-3168. ISSN 2155-5435

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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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
Keywords:Acetoxylation; DFT; Meta-C−H Activation; Olefination; Palladium
ID Code:109680
Deposited On:02 Aug 2017 08:24
Last Modified:02 Aug 2017 08:24

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