Recent Advances in C–F Bond Activation of Acyl Fluorides Directed toward Catalytic Transformation by Transition Metals, N-Heterocyclic Carbenes, or Phosphines

Abstract

Numerous studies on the activation of carbon–fluorine bonds have been reported in recent years. For example, acyl fluorides have been utilized as versatile reagents for acylation, arylation, and even fluorination. In this review, we focus on acyl fluorides as compounds with carbon–fluorine bonds, and highlight recent advances in strategies for the activation of their C–F bonds via transition-metal catalysis, N-heterocyclic carbene (NHCs) catalysis, organophosphine catalysis, and classical nucleophilic substitution reactions.

1 Introduction

2 Transition-Metal-Mediated C–F Bond Activation

2.1 Acylation (Carbonyl-Retentive) Coupling Reactions

2.2 Decarbonylative Reactions

2.3 C–F Bond Activation by Other Transition Metals

3 C–F Bond Activation by N-Heterocyclic Carbenes (NHCs)

3.1 NHC-Catalyzed Cycloaddition of Acyl Fluorides

3.2 NHC-Catalyzed Radical Functionalization of Acyl Fluorides

3.3 NHC-Catalyzed Nucleophilic Fluorination of (Hetero)aromatics

4 C–F Bond Activation by Phosphines

4.1 Phosphine-Catalyzed Direct Activation of the C–F Bond of Acyl Fluorides

4.2 Phosphine-Catalyzed Indirect Activation of the C–F Bond of Acyl Fluorides

5 C–F Bond Activation by Classical Nucleophilic Substitution

6 Miscellaneous Examples

7 Summary and Perspective

Key words

acyl fluorides - C–F bond activation - transition metals - N-heterocyclic carbenes - organophosphines

Publication History

Received: 31 March 2022

Accepted after revision: 06 May 2022

Accepted Manuscript online:
06 May 2022

Article published online:
30 June 2022

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