Acyl Fluorides in Late-Transition-Metal Catalysis

Research output: Contribution to journalReview article

4 Citations (Scopus)

Abstract

In this Review, we summarize the current state of the art in late-transition-metal-catalyzed reactions of acyl fluorides, covering both their synthesis and further transformations. In organic reactions, the relationship between stability and reactivity of the starting substrates is usually characterized by a trade-off. Yet, acyl fluorides display a very good balance between these properties, which is mostly due to their moderate electrophilicity. Thus, acyl fluorides (RCOF) can be used as versatile building blocks in transition-metal-catalyzed reactions, for example, as an “RCO” source in acyl coupling reactions, as an “R” source in decarbonylative coupling reactions, and as an “F” source in fluorination reactions. Starting from the cleavage of the acyl C−F bond in acyl fluorides, various transformations are accessible, including C−C, C−H, C−B, and C−F bond-forming reactions that are catalyzed by transition-metal catalysts that contain the Group 9–11 metals Co, Rh, Ir, Ni, Pd, or Cu.

Original languageEnglish
Pages (from-to)574-594
Number of pages21
JournalAngewandte Chemie - International Edition
Volume59
Issue number2
DOIs
Publication statusPublished - 7 Jan 2020

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Fluorides
Catalysis
Transition metals
Fluorination
Catalysts
Metals
Substrates

Keywords

  • acyl fluorides
  • cross-coupling
  • homogeneous catalysis
  • transition metals
  • versatile building blocks

Cite this

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Acyl Fluorides in Late-Transition-Metal Catalysis. / Ogiwara, Yohei; Sakai, Norio.

In: Angewandte Chemie - International Edition, Vol. 59, No. 2, 07.01.2020, p. 574-594.

Research output: Contribution to journalReview article

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AU - Sakai, Norio

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AB - In this Review, we summarize the current state of the art in late-transition-metal-catalyzed reactions of acyl fluorides, covering both their synthesis and further transformations. In organic reactions, the relationship between stability and reactivity of the starting substrates is usually characterized by a trade-off. Yet, acyl fluorides display a very good balance between these properties, which is mostly due to their moderate electrophilicity. Thus, acyl fluorides (RCOF) can be used as versatile building blocks in transition-metal-catalyzed reactions, for example, as an “RCO” source in acyl coupling reactions, as an “R” source in decarbonylative coupling reactions, and as an “F” source in fluorination reactions. Starting from the cleavage of the acyl C−F bond in acyl fluorides, various transformations are accessible, including C−C, C−H, C−B, and C−F bond-forming reactions that are catalyzed by transition-metal catalysts that contain the Group 9–11 metals Co, Rh, Ir, Ni, Pd, or Cu.

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