Inorganic Chemistry

Photoinduced Dehydrogenative Borylation via Dihydrogen Bond Bridged Electron Donor and Acceptor Complexes

Authors

  • Zhiyong Wang The Hong Kong University of Science and Technology ,
  • Jiaxin Chen The Hong Kong University of Science and Technology ,
  • Zhenyang Lin The Hong Kong University of Science and Technology ,
  • Yangjian QUAN The Hong Kong University of Science and Technology

Abstract

Air-stable amine- and phosphine-boranes are discovered as donors to integrate with pyridinium acceptor for generating pho-toactive electron-donor-acceptor (EDA) complexes. Experimental results and DFT calculations suggest a dihydrogen bond bridging the donor and acceptor. Illuminating the EDA complex enables an intramolecular single electron transfer to give boron-centered radical for dehydrogenative borylation with no need of external photosensitizer and oxidant. The deproto-nation of Wheland-like radical intermediate rather than its generation is believed to determine the very good ortho-selectivity based on DFT calculations. A variety of α-borylated pyridine derivatives have been readily synthesized with good functional group tolerance.

Content

Thumbnail image of TEXT.pdf

Supplementary material

Thumbnail image of SI.pdf
SI
Experimental procedures, DFT calculation details, and characterization of the products