Article, 2024

Mechanochemical Synthesis of Trifluoromethyl Arenes: Nanocellulose-Supported Deaminative Trifluoromethylation of Aromatic Amines

ACS Sustainable Chemistry & Engineering, ISSN 2168-0485, Volume 12, 24, Pages 8980-8989, 10.1021/acssuschemeng.4c00846

Contributors

Mkrtchyan, Satenik 0009-0000-6841-5622 (Corresponding author) [1] Purohit, Vishal B 0000-0002-9392-8136 [2] Shalimov, Oleksandr O 0000-0002-1538-3206 [3] Zapletal, Jiří [1] Sarfaraz, Sehrish [4] Ayub, Khurshid 0000-0003-0990-1860 [4] Filo, Juraj 0000-0002-3995-2565 [5] Sillanpää, Mika Erik Tapio 0000-0003-3247-5337 [6] [7] Skoršepa, Marek 0000-0003-0996-9152 [1] Iaroshenko, Viktor O 0000-0002-5647-5326 (Corresponding author) [1] [8] [9] [10]

Affiliations

  1. [1] Matej Bel University
    2. [NORA names: Slovakia; Europe, EU; OECD];
  2. [2] Charotar University of Science and Technology
    3. [NORA names: India; Asia, South];
  3. [3] Institute of Organic Chemistry
    4. [NORA names: Ukraine; Europe, Non-EU];
  4. [4] COMSATS University Islamabad
    5. [NORA names: Pakistan; Asia, South];
  5. [5] Comenius University
    6. [NORA names: Slovakia; Europe, EU; OECD];

Abstract

A convenient one-pot procedure for the mechanochemical nanocellulose-supported synthesis of trifluoromethyl arenes has been developed through the selective transformation of an aromatic amino group into the trifluoromethyl functionality using pyrylium tetrafluoroborate (Pyry-BF4) and trifluoromethyl­trimethylsilane (TMSCF3) via in situ formation of the pyridinium salt intermediate under transition metal-free conditions. The nanocellulose acts here as a green reaction medium, and the reaction does not occur without this additive. The scope of the present protocol includes synthesis of 28 trifluoromethyl arenes in excellent yields via a selective (ipso-)­substitution (SNAr) of aromatic amino group with CF3 functionality. This method could have a great significance in pharmaceutical industries for the late-stage functionalization of active pharmaceutical ingredients (APIs)/drugs.

Keywords

CF3, CF3 functionality, Mechanochemical, SNAr, TMSCF3, amines, amino groups, arenes, aromatic amines, aromatic amino group, conditions, excellent yields, formation, function, green reaction medium, group, in situ formation, industry, intermediate, late-stage functionalization, medium, metal-free conditions, method, nanocellulose, one-pot procedure, pharmaceutical industry, procedure, protocol, pyridinium, pyridinium salt intermediates, pyrylium, reaction, reaction medium, significance, synthesis, tetrafluoroborate, transformation, transition, transition metal-free conditions, trifluoromethyl, trifluoromethyl functionality, trifluoromethylated arenes, trifluoromethyltrimethylsilane, yield

Funders

  • Knut and Alice Wallenberg Foundation
  • Slovak Research and Development Agency

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