1.8 Synthesis of (Trifluoromethyl)sulfanyl (SCF3) Compounds

C. Xu; X. Shao; Q. Shen

doi:10.1055/sos-SD-243-00266

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Paquin, J.-F. : 2024 Science of Synthesis, 2024/4: Modern Strategies in Organofluorine Chemistry 1 DOI: 10.1055/sos-SD-243-00266

Modern Strategies in Organofluorine Chemistry 1

1.8 Synthesis of (Trifluoromethyl)sulfanyl (SCF₃) Compounds

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Editor: Paquin, J.-F.

Authors: Arimitsu, S. ; Barata-Vallejo, S. ; Brioche, J. ; Cahard, D. ; Charette, A. B. ; Chen, P. ; Crousse, B. ; De Borggraeve, W. M. ; Hu, M. ; Ismalaj, E. ; Joosten, A. ; Kordnezhadian, R. ; Lai, J. ; Liu, G. ; Luo, Y.-C. ; Peyrical, L. C. ; Postigo, A. ; Sammis, G. M. ; Shao, X. ; Shen, Q. ; Song, H.; Thomson, B. J. ; Wu, S.; Xu, C. ; Yerien, D. E. ; Zhang, X.

Title: Modern Strategies in Organofluorine Chemistry 1

Online ISBN: 9783132458253; Book DOI: 10.1055/b000000921

1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

(Trifluoromethyl)sulfanyl compounds have garnered significant attention in medicinal chemistry, agrochemistry, and materials science due to their unique physicochemical properties, including high lipophilicity, metabolic stability, and strong electron-withdrawing ability. This review pro-vides a comprehensive overview of the current methods for the synthesis of (trifluoromethyl)sulfanyl compounds, highlighting recent advances and emerging strategies. Key synthetic approaches, such as direct (trifluoromethyl)sulfanylation, transition-metal-catalyzed processes, and radical-based methods are discussed with an emphasis on the substrates and reagents. The chapter also briefly introduces the mechanistic insights and the role of novel reagents in enhancing the efficiency and selectivity of these synthetic transformations.

Key words

(trifluoromethyl)sulfanyl compounds - electrophilic (trifluoromethyl)sulfanylation - nucleophilic (trifluoromethyl)sulfanylation - radical (trifluoromethyl)sulfanylation - (difluoro-methyl)sulfanylation - fluorinated alkyl thioethers - (fluoroalkyl)sulfanyl compounds - palladium catalysis - photocatalysis - carbon–sulfur bond formation - nitrogen–sulfur bond formation - oxygen–sulfur bond formation - asymmetric (trifluoromethyl)sulfanylation

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