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

Uttam Dutta, Atanu Modak, Bangaru Bhaskararao, Milan Bera, Sukdev Bag, Anirban Mondal, David W. Lupton, Raghavan B. Sunoj, Debabrata Maiti

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33 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3162-3168
Number of pages7
JournalACS Catalysis
Volume7
Issue number5
DOIs
Publication statusPublished - 5 May 2017

Keywords

  • acetoxylation
  • DFT
  • meta-C-H activation
  • olefination
  • palladium

Cite this

Dutta, U., Modak, A., Bhaskararao, B., Bera, M., Bag, S., Mondal, A., Lupton, D. W., Sunoj, R. B., & Maiti, D. (2017). Catalytic Arene meta-C-H Functionalization Exploiting a Quinoline-Based Template. ACS Catalysis, 7(5), 3162-3168. https://doi.org/10.1021/acscatal.7b00247