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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| Published in | Journal of the American Chemical Society Vol. 143; no. 33; pp. 13029 - 13033 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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25.08.2021
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| Abstract | 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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| AbstractList | 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. |
| Author | Schoenebeck, Franziska Zivkovic, Filip G Nielsen, Christian D.-T |
| AuthorAffiliation | Institute of Organic Chemistry |
| AuthorAffiliation_xml | – name: Institute of Organic Chemistry |
| Author_xml | – sequence: 1 givenname: Christian D.-T surname: Nielsen fullname: Nielsen, Christian D.-T – sequence: 2 givenname: Filip G surname: Zivkovic fullname: Zivkovic, Filip G – sequence: 3 givenname: Franziska orcidid: 0000-0003-0047-0929 surname: Schoenebeck fullname: Schoenebeck, Franziska email: franziska.schoenebeck@rwth-aachen.de |
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| Title | Synthesis of N‑CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N‑CF3 Carbamoyl Fluorides |
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