Unlocking the Power of Acyl Fluorides: A Comprehensive Guide to Synthesis and Properties

被引:10
作者
Bonnefoy, Clemence [1 ]
Gallego, Adrien [1 ,2 ]
Delobel, Clement [1 ]
Raynal, Betty [2 ]
Decourt, Maxime [2 ]
Chefdeville, Emmanuel [3 ]
Hanquet, Gilles [4 ]
Panossian, Armen [4 ]
Leroux, Frederic R. [4 ]
Toulgoat, Fabien [1 ,2 ]
Billard, Thierry [1 ]
机构
[1] Univ Lyon 1, Inst Chem & Biochem, CPE Lyon, CNRS,UMR 5246, 1 Rue Victor Grignard, F-69622 Lyon, France
[2] CPE Lyon Campus LyonTech La Doua, 43 Bd 11 Novembre 1918, F-69616 Villeurbanne, France
[3] Univ Lyon 1, NMR Ctr, CNRS, 1 Rue Victor Grignard, F-69622 Lyon, France
[4] Univ Haute Alsace, Univ Strasbourg, CNRS, UMR 7042,LIMA,ECPM, F-67000 Strasbourg, France
关键词
acyl fluoride; amide; trifluoromethoxide; acyl chloride; 2,4-dinitrotrifluoromethoxybenzene; AMINO-ACID FLUORIDES; AMIDE BOND FORMATION; CARBOXYLIC-ACIDS; REAGENTS; DEOXYFLUORINATION; FLUORINATION; CONVENIENT; ACCESS;
D O I
10.1002/ejoc.202400142
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acyl fluorides have emerged as versatile reagents in various synthetic endeavors, offering a range of advantages over their counterparts, acyl chlorides. This study delves into the properties and reactivity of acyl fluorides, particularly their reaction with amines and alcohols, to elucidate their distinct characteristics. We also introduce a facile and practical synthesis of acyl fluorides from a stable solution of CF3O- salt. Additionally, we establish an efficient one-pot process for the direct preparation of amides or esters from corresponding acids and amines or alcohols, showcasing the remarkable efficiency of acyl fluorides in these transformations. The facile and safe synthesis of acyl fluorides, under metal-free and cost-effective conditions, presents a remarkable advance in organic synthesis. These versatile reagents, endowed with distinct reactivity owing to the fluorine atom, offer a wealth of possibilities for further utilization. image
引用
收藏
页数:7
相关论文
共 86 条
[1]   Fe3+-exchanged clay catalyzed transamidation of amides with amines under solvent-free condition [J].
Ali, Md. Ayub ;
Siddiki, S. M. A. Hakim ;
Kon, Kenichi ;
Shimizu, Ken-ichi .
TETRAHEDRON LETTERS, 2014, 55 (07) :1316-1319
[2]   Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C-N Bond Cleavage [J].
Aliyu Idris, Muhammad ;
Song, Kwang Ho ;
Lee, Sunwoo .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) :2449-2453
[3]  
Ameduri B, 2020, Fascinating Fluoropolymers and Their Applications, V2, P474
[4]   C-F Bond Activation in Organic Synthesis [J].
Amii, Hideki ;
Uneyama, Kenji .
CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183
[5]   Synthesis and biological evaluation of nonpeptide mimetics of co-conotoxin GVIA [J].
Baell, JB ;
Duggan, PJ ;
Forsyth, SA ;
Lewis, RJ ;
Lok, YP ;
Schroeder, CI .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :4025-4037
[6]   Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents [J].
Beaulieu, Francis ;
Beauregard, Louis-Philippe ;
Courchesne, Gabriel ;
Couturier, Michel ;
LaFlamme, Francois ;
L'Heureux, Alexandre .
ORGANIC LETTERS, 2009, 11 (21) :5050-5053
[7]   Organic fluorine compounds: a great opportunity for enhanced materials properties [J].
Berger, Ricarda ;
Resnati, Giuseppe ;
Metrangolo, Pierangelo ;
Weber, Edwin ;
Hulliger, Juerg .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3496-3508
[8]   The Use of Fluoride as a Leaving Group: SN2' Displacement of a C?F Bond on 3,3-Difluoropropenes with Organolithium Reagents To Give Direct Access to Monofluoroalkenes [J].
Bergeron, Maxime ;
Johnson, Thomas ;
Paquin, Jean-Francois .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11112-11116
[9]  
Billard T., 2023, 26 WINTER FLUORINE C
[10]   Acid Fluorides in Transition-Metal Catalysis: A Good Balance between Stability and Reactivity [J].
Blanchard, Nicolas ;
Bizet, Vincent .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (21) :6814-6817