4.8 Article

Upgrading ketone synthesis direct from carboxylic acids and organohalides

Journal

NATURE COMMUNICATIONS
Volume 11, Issue 1, Pages -

Publisher

NATURE PUBLISHING GROUP
DOI: 10.1038/s41467-020-17224-2

Keywords

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Funding

  1. National Natural Science Foundation of China [21971108, 21971111, 21702098, 21732003, 21672099]
  2. Natural Science Foundation of Jiangsu Province [BK20190006]
  3. Fundamental Research Funds for the Central Universities [020514380214]
  4. Innovation & Entrepreneurship Talents Plan of Jiangsu Province
  5. 1000-Youth Talents Plan
  6. Jiangsu Six Peak Talent Project
  7. Nanjing University

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The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals. Due to their abundance and importance in organic chemistry, development of methods for ketone synthesis is essential. Here, the authors report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of aromatic acids and aryl/alkyl bromides to directly synthesise ketones.

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