4.8 Article

Electrochemical Benzylic C(sp3)-H Isothiocyanation

Journal

ORGANIC LETTERS
Volume 24, Issue 8, Pages 1742-1746

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00415

Keywords

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Funding

  1. Natural Science Foundation of Shandong Province [ZR2020MB005, ZR2019MB010]
  2. Talent Fund for Province and Ministry Co-construction Collaborative Innovation Center of Eco-Chemical Engineering [XTCXYX04]

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In this study, we report an electrochemical benzylic isothiocyanation method with high chemoselectivity and site-selectivity under oxidant-free conditions. The method is notable for its compatibility with functional groups and its suitability for late-stage functionalization of bioactive molecules.
Selective C(sp(3))-H isothiocyanation represents a significant strategy for the synthesis of isothiocyanate derivatives. We report herein an electrochemical benzylic isothiocyanation in a highly chemo- and site-selective manner under external oxidant-free conditions. The high chemoselectivity is attributed to the facile in situ isomerization of benzylic thiocyanates to isothiocyanates. Notably, the method exhibits high functional group compatibility and is suitable for late-stage functionalization of bioactive molecules.

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