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

[41] 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
Ammon, HL
STRUCTURAL CHEMISTRY, 2001, 12 (3-4) : 205 - 212
[42] Reliable Quantum-Chemistry Heats of Formation for an Extensive Set of C-, H-, N-, O-, F-, S-, Cl-, Br-Containing Molecules in the NIST Chemistry Webbook
Chan, Bun
JOURNAL OF PHYSICAL CHEMISTRY A, 2025,
[43] Synthetic utilization of polynitro aromatic compounds.: 5.: Multi-centered reactivity pattern in reactions of 4,6-dinitro-1,2-benzisothiazoles and -isothiazol-3(2H)-ones with C-, N-, O-, S-, and F-nucleophiles
Zlotin, Sergei G.
Kislitsin, Pavel G.
Kucherov, Fedor A.
Serebryakov, Evgeny A.
Strelenko, Yury A.
Gakh, Andrei A.
HETEROCYCLES, 2006, 68 (12) : 2483 - 2498
[44] Analysis of C1s Spectra of N-, O-, and X-Containing Polymers in X-Ray Photoelectron Spectroscopy by ab initio Molecular Orbital Calculations Using Model Molecules
Kazunaka Endo
Shigehiro Maeda
Yasuo Kaneda
Polymer Journal, 1997, 29 : 255 - 260
[45] Analysis of C1s spectra of N-, O-, and X-containing polymers in X-ray photoelectron spectroscopy by ab initio molecular orbital calculations using model molecules
Endo, K
Maeda, S
Kaneda, Y
POLYMER JOURNAL, 1997, 29 (03) : 255 - 260
[46] Syntheses and 1H, 13C, 15N, 17O, 205Tl NMR of new ring-functionalised chelating half-sandwich complexes of thallium(I) containing an N-, O- or S-donor atom
Tromp, DS
Frühauf, HW
Elsevier, CJ
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2005, 70 (10) : 1604 - 1614
[47] Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles:: VII.: Reaction of 1-chloroalkyl isocyanates with N,N-disubstituted cyanothioacetamides.: A new synthetic route to 6-dialkylamino-4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitriles
Sukach, V. A.
Chubaruk, N. G.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (04) : 553 - 558
[48] Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: VII. Reaction of 1-chloroalkyl isocyanates with N,N-disubstituted cyanothioacetamides. A new synthetic route to 6-dialkylamino-4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitriles
V. A. Sukach
N. G. Chubaruk
M. V. Vovk
Russian Journal of Organic Chemistry, 2007, 43 : 553 - 558

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