Synthesis of N‑CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N‑CF3 Carbamoyl Fluorides

The expansion of chemical space associated with ubiquitous motifs is key to unleash new properties and functions. In this context, alkynamides, prevalent in numerous drugs and materials, represent an untapped resource. We herein report the first synthetic access to N-trifluoromethyl alkynamides. Our...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 143; no. 33; pp. 13029 - 13033
Main Authors Nielsen, Christian D.-T, Zivkovic, Filip G, Schoenebeck, Franziska
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.08.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CHEMISTRY
CANDIDATE
INHIBITORS
ACID FLUORIDES
DISCOVERY
AMIDES
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Summary:The expansion of chemical space associated with ubiquitous motifs is key to unleash new properties and functions. In this context, alkynamides, prevalent in numerous drugs and materials, represent an untapped resource. We herein report the first synthetic access to N-trifluoromethyl alkynamides. Our strategy relies on a mild and operationally simple Ni-catalyzed coupling of N-CF3 carbamoyl fluorides with alkynyl silanes. The synthesized N-CF3 alkynamides proved to be highly robust and readily functioned as a platform to unlock access to valuable derivatives, such as N-CF3 decorated alkenyl amides, oxindoles, or quinolones, all of which were inaccessible to date.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c07780