4.8 Article

Hydrogen-Atom Transfer Catalysis for C-H Alkylation of Benzylic Fluorides

Journal

ORGANIC LETTERS
Volume 24, Issue 17, Pages 3134-3137

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00817

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Funding

  1. JSPS KAKENHI [JP17H06446, JP21H01930]
  2. JSPS

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In this study, a photoinduced catalytic C(sp3)-H alkylation of benzylic fluorides was developed. The use of zwitterionic 1,2,3-triazolium amidate as a hydrogen-atom transfer catalyst proved uniquely effective for promoting this transformation, enabling 1,1-difunctionalization of benzylic fluorides and providing rapid access to a variety of functionalized molecular entities.
A photoinduced catalytic C(sp3)-H alkylation of benzylicfluorides is developed. The use of zwitterionic 1,2,3-triazolium amidate as ahydrogen-atom transfer catalyst is uniquely effective for promoting thistransformation. The combination of C-H alkylation with subsequentdisplacement of the C-F bond enables 1,1-difunctionalization of benzylicfluorides, providing rapid access to an array of functionalized molecularentities

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