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

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...

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Bibliographic Details
Published inACS catalysis Vol. 7; no. 5; pp. 3162 - 3168
Main Authors Dutta, Uttam, Modak, Atanu, Bhaskararao, Bangaru, Bera, Milan, Bag, Sukdev, Mondal, Anirban, Lupton, David W, Sunoj, Raghavan B, Maiti, Debabrata
Format Journal Article
LanguageEnglish
Published American Chemical Society 05.05.2017
Subjects
palladium
meta-C−H activation
DFT
acetoxylation
olefination
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.7b00247