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

Chemistry (Weinheim an der Bergstrasse, Germany)(2022)

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