Electricity-driven asymmetric bromocyclization enabled by chiral phosphate anion phase-transfer catalysis

Xuefeng Tan (), Qingli Wang and Jianwei Sun ()
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Xuefeng Tan: The Hong Kong University of Science and Technology (HKUST)
Qingli Wang: The Hong Kong University of Science and Technology (HKUST)
Jianwei Sun: The Hong Kong University of Science and Technology (HKUST)

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Electricity-driven asymmetric catalysis is an emerging powerful tool in organic synthesis. However, asymmetric induction so far has mainly relied on forming strong bonds with a chiral catalyst. Asymmetry induced by weak interactions with a chiral catalyst in an electrochemical medium remains challenging due to compatibility issues related to solvent polarity, electrolyte interference, etc. Enabled by a properly designed phase-transfer strategy, here we have achieved two efficient electricity-driven catalytic asymmetric bromocyclization processes induced by weak ion-pairing interaction. The combined use of a phase-transfer catalyst and a chiral phosphate catalyst, together with NaBr as the bromine source, constitutes the key advantages over the conventional chemical oxidation approach. Synergy over multiple events, including anodic oxidation, ion exchange, phase transfer, asymmetric bromination, and inhibition of Br2 decomposition by NaHCO3, proved critical to the success.

Date: 2023
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DOI: 10.1038/s41467-023-36000-6

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