Trifluoromethoxylation Reactions of (Hetero) arenes, Olefinic Systems and Aliphatic Saturated Substrates

被引:22
作者
Barata-Vallejo, Sebastian [1 ,3 ]
Bonesi, Sergio M. [2 ]
Postigo, Al [1 ]
机构
[1] Univ Buenos Aires, Fac Farm & Bioquim, Dept Ciencias Quim, Junin 954, RA-1113 Buenos Aires, DF, Argentina
[2] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, Ciudad Univ,C1428EGA, Buenos Aires, DF, Argentina
[3] CNR, Ist Sintesi Organ & Fotoreatt ISOF, Via P Gobetti 101, I-40129 Bologna, Italy
关键词
carbon-carbon multiple bonds; (hetero)arenes; redox-neutral radical reaction; substitution at Csp(3); trifluoromethoxylation; SUBSTITUENT CONSTANTS; TRIFLUOROMETHYLATION; ETHERS; FLUORODECARBOXYLATION; (HETERO)ARENES; FLUORINATION; REACTIVITY; RESONANCE; ALKENES; ACCESS;
D O I
10.1002/chem.202201776
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct fluoroalkoxylation reactions of (hetero)arenes, carbon-carbon multiple bonds, and substitution reactions at Csp(3) carbon centers by CF3O, CHF2O, and (CF3)(2)CFO groups are discussed. Emphasis on thermal radical, electron transfer, photocatalytic, electrochemical and redox-neutral radical methods are placed to accomplish fluoroalkoxylation reactions. All these methods employ either radical fluoroalkoxylating reagents or some nucleophilic trifluoromethoxylating sources of CF3O. A summary of all these methods is provided in Table 2.
引用
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页数:18
相关论文
共 102 条
[1]   ALPHA-FLUORINATED ETHERS .2. ALKYL FLUOROALKYL ETHERS [J].
ALDRICH, PE ;
SHEPPARD, WA .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (01) :11-&
[2]  
[Anonymous], 2016, ANGEW CHEM, V128, P9910
[3]  
[Anonymous], 2020, Angew. Chem, V132, P21659
[4]  
[Anonymous], 2014, ANGEW CHEM, V126, P14787
[5]  
[Anonymous], 2016, ANGEW CHEM, V128, P11900
[6]  
[Anonymous], 2015, ANGEW CHEM, V127, P12005
[7]  
[Anonymous], 2019, ANGEW CHEM, V131, P7922
[8]   Study of a Stable "Trifluoromethoxide Anion Solution" Arising from 2,4-Dinitro-Trifluoromethoxybenzene [J].
Bonnefoy, Clemence ;
Chefdeville, Emmanuel ;
Panosian, Armen ;
Hanquet, Gilles ;
Leroux, Frederic R. ;
Toulgoat, Fabien ;
Billard, Thierry .
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (64) :15986-15991
[9]   Isolation and Reactivity of Trifluoromethyl Iodonium Salts [J].
Brantley, Johnathan N. ;
Samant, Andrew V. ;
Toste, F. Dean .
ACS CENTRAL SCIENCE, 2016, 2 (05) :341-350
[10]   Xenon Difluoride Mediated Fluorodecarboxylations for the Syntheses of Di- and Trifluoromethoxyarenes [J].
Chatalova-Sazepin, Claire ;
Binayeva, Meruyert ;
Epifanov, Maxim ;
Zhang, Wei ;
Foth, Paul ;
Amador, Carolyn ;
Jagdeo, Manu ;
Boswell, Benjamin R. ;
Sammis, Glenn M. .
ORGANIC LETTERS, 2016, 18 (18) :4570-4573