Difluoromethylation of O-, S-, N-, C-Nucleophiles Using Difluoromethyltri(n-butyl)ammonium Chloride as a New Difluorocarbene Source

被引：74

作者：

Wang Fei ^{[1
]}

Huang Weizhou ^{[1
]}

Hu Jinbo ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2011年 / 29卷 / 12期

基金：

中国国家自然科学基金;

关键词：

difluorocarbene; CF2H group; difluoromethylation; difluoromethyltri(n-butyl)ammonium chloride; GEM-DIFLUOROCYCLOPROPANES; REAGENT; KETONES; CYCLOPROPANES; THIOETHERS; ETHERS; SALTS; TFDA;

D O I：

10.1002/cjoc.201100325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Difluoromethyltri(n-butyl)ammonium chloride 1 was found to be an effective difluorocarbene reagent for O-, S-, N-, C-difluoromethylation under basic conditions. It is particularly remarkable that, when only 1.2 equivalent of reagent 1 was used, the difluoromethylated products were obtained in moderate to excellent yields.

引用

页码：2717 / 2721

页数：5

共 48 条

[31] Ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate in reactions with O-, S-, N-, and P-nucleophiles
Maadadi, R.
Pevzner, L. M.
Petrov, M. L.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (11) : 2462 - 2468
[32] Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement
Chen, Peiran
Su, Jie
TETRAHEDRON, 2016, 72 (01) : 84 - 94
[33] Ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate in reactions with O-, S-, N-, and P-nucleophiles
R. Maadadi
L. M. Pevzner
M. L. Petrov
Russian Journal of General Chemistry, 2016, 86 : 2462 - 2468
[34] Regio- and Stereoselective (SN2) N-, O-, C- and S-Alkylation Using Trialkyl Phosphates
Banerjee, Amit
Hattori, Tomohiro
Yamamoto, Hisashi
SYNTHESIS-STUTTGART, 2023, 55 (02): : 315 - 332
[35] Anticancer Tungstenocenes with a Diverse Set of (O,O-), (O,S-) and (O,N-) Chelates-A Detailed Biological Study Using an Improved Evaluation via 3D Spheroid Models
Cseh, Klaudia
Berasaluce, Iker
Fuchs, Valentin
Banc, Alexandra
Schweikert, Andreas
Prado-Roller, Alexander
Hejl, Michaela
Wernitznig, Debora
Koellensperger, Gunda
Jakupec, Michael A.
Kandioller, Wolfgang
Malarek, Michael S.
Keppler, Bernhard K.
PHARMACEUTICS, 2023, 15 (07)
[36] Comparing B-H Bond Activation in NiIIX(NNN)-Catalyzed Nitrile Dihydroboration (X = Anionic N-, C-, O-, S-, or P-donor)
Ataie, Saeed
Baker, R. Tom
INORGANIC CHEMISTRY, 2022, 61 (49) : 19998 - 20007
[37] Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis
Garnier, Tony
Danel, Mathieu
Magne, Valentin
Pujol, Anthony
Beneteau, Valerie
Pale, Patrick
Chassaing, Stefan
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6408 - 6422
[38] Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: X. 1-Chloroalkyl isocyanates in the synthesis of new 5-aroyldihydropyrimidines
O. V. Kushnir
V. A. Sukach
M. V. Vovk
Russian Journal of Organic Chemistry, 2009, 45 : 755 - 761
[39] Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: X. 1-Chloroalkyl isocyanates in the synthesis of new 5-aroyldihydropyrimidines
Kushnir, O. V.
Sukach, V. A.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (05) : 755 - 761
[40] New Atom/Functional Group Volume Additivity Data Bases for the Calculation of the Crystal Densities of C-, H-, N-, O-, F-, S-, P-, Cl-, and Br-Containing Compounds
Herman L. Ammon
Structural Chemistry, 2001, 12 : 205 - 212

← 1 2 3 4 5 →