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

Tian Tian; Qiang Chen; Zhiping Li; Yasushi Nishihara

doi:10.1055/a-1845-3810

Synthesis, Table of Contents

Synthesis 2022; 54(17): 3667-3697
DOI: 10.1055/a-1845-3810

review

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

Tian Tian

^aGraduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

,

Qiang Chen

^aGraduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

,

Zhiping Li

^bDepartment of Chemistry, Renmin University of China, Beijing 100872, P. R. of China

,

Yasushi Nishihara ∗

^cResearch Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

› Author Affiliations

Abstract

All articles of this category

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

Full Text

References

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