Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Jingjing Wu, Robin Baer, Lin Guo, Adam Noble, Varinder Kumar Aggarwal

Research output: Contribution to journal › Article (Academic Journal)

11 Citations (Scopus)

Abstract

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2‐iodophenyl‐thionocarbonate enables a novel Barton‐McCombie‐type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.
Original languageEnglish
Number of pages6
JournalAngewandte Chemie - International Edition
Early online date15 Oct 2019
DOIs
Publication statusE-pub ahead of print - 15 Oct 2019

Keywords

  • Boronsäureester
  • Borylierungen
  • Desoxygenierung
  • Photochemie
  • Radikalreaktionen

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  • Full-text PDF (accepted author manuscript)

    This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/10.1002/ange.201910051. Please refer to any applicable terms of use of the publisher.

    Accepted author manuscript, 1.14 MB

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    • Projects

    FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

    Aggarwal, V. K.

    1/10/15 → 31/03/21

    Project: Research

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