4.8 Article

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

Journal

CHEMICAL SCIENCE
Volume 7, Issue 6, Pages 3676-3680

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc04521e

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Funding

  1. NSFC [21472146]
  2. Department of Science and Technology of Shaanxi Province [2015KJXX-02]
  3. Ministry of Science and Technology of the People's Republic of China [2014CB548200]

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A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.

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