Photochemical Synthesis of Acyl Fluorides Using Copper-Catalyzed Fluorocarbonylation of Alkyl Iodides

被引:3
作者
Tung, Pinku [1 ]
Mankad, Neal P. [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
关键词
ACID FLUORIDE; CARBONYLATION; ACCESS;
D O I
10.1021/acs.orglett.4c00967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acyl fluorides are important reagents due to their unique balance between reactivity and stability. Here, we report a copper-catalyzed carbonylative coupling strategy for synthesizing acyl fluorides under photoirradiation. Alkyl iodides were transformed in high yields into acyl fluorides by using a commercially available copper precatalyst (CuBr center dot SMe2) and a readily available fluoride salt (KF) at ambient temperature and mild CO pressure (6 atm) under blue light irradiation.
引用
收藏
页码:3299 / 3303
页数:5
相关论文
共 50 条
[31]   Copper-Catalyzed Fluoroalkylphosphorothiolation of Alkynes for the Synthesis of (E)-β-Fluoroalkyl Vinyl Phosphorothioates [J].
Shi, Shanshan ;
Chen, Hu ;
Zhao, Ming ;
Yang, Shiwei ;
Li, Pan ;
Wang, Xiaohong ;
Zhu, Jinmiao ;
Fang, Qi ;
Xu, Wenbiao ;
Tang, Guo ;
Gao, Yuzhen .
ORGANIC LETTERS, 2023, 25 (46) :8296-8301
[32]   Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes [J].
Erickson, Lucas W. ;
Lucas, Erika L. ;
Tollefson, Emily J. ;
Jarvo, Elizabeth R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (42) :14006-14011
[33]   Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles [J].
Ye, Changqing ;
Li, Yajun ;
Zhu, Xiaotao ;
Hu, Shengmin ;
Yuan, Daqiang ;
Bao, Hongli .
CHEMICAL SCIENCE, 2019, 10 (12) :3632-3636
[34]   Copper-catalyzed synthesis of alkynylphosphine derivatives: unprecedented use of nucleophilic phosphorus compounds [J].
Bernoud, Elise ;
Alayrac, Carole ;
Delacroix, Olivier ;
Gaumont, Annie-Claude .
CHEMICAL COMMUNICATIONS, 2011, 47 (11) :3239-3241
[35]   Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines [J].
Zorba, Leandros P. ;
Stylianakis, Ioannis ;
Tsoureas, Nikolaos ;
Kolocouris, Antonios ;
Vougioukalakis, Georgios C. .
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11) :7727-7740
[36]   Synthesis of Sulfoximines by Copper-Catalyzed Oxidative Coupling of Sulfinamides and Aryl Boronic Acids [J].
Zou, Xi ;
Wang, Hanbing ;
Gao, Bing .
ORGANIC LETTERS, 2023, :7656-7660
[37]   Synthesis of Mono-fluoroallenes through Copper-Catalyzed Defluorinative Silylation of α,α-Difluoroalkylalkynes [J].
Tang, Luning ;
Pei, Bing-Bing ;
Song, Yang ;
Xue, Fei ;
Yue, Yanni ;
Feng, Chao .
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (17) :2035-2039
[38]   Copper-Catalyzed Cross Coupling Reaction of Alkyl Bromides with (DMPU)2Zn(Rf)2 Reagent: A Method for the Synthesis of Perfluoroalkylated Compounds [J].
Liu, Bosheng ;
Jiang, Xujuan ;
Song, Yanshan ;
Liu, Shiwen ;
Xiong, Xiaodong ;
Zeng, Xiaojun .
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (24) :5001-5007
[39]   One-Step Synthesis of Acylborons from Acyl Chlorides through Copper-Catalyzed Borylation with Polystyrene-Supported PPh3 Ligand [J].
Nakahara, Masataka ;
Kurahayashi, Kazuki ;
Hanaya, Kengo ;
Sugai, Takeshi ;
Higashibayashi, Shuhei .
ORGANIC LETTERS, 2022, 24 (30) :5596-5601
[40]   Copper-Catalyzed Electrophilic Arylation of Isatoic Anhydride with Diaryliodonium Salts for Synthesis of N-Phenylated Isatoic Anhydrides [J].
Wu, Xi-Xi ;
He, Yonghui ;
Zhao, Xiao-Jing ;
Li, Ganpeng .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (07)