Reactions of some nitrogen heterocycles with chlorodifluoromethane under conditions of phase-transfer catalysis

Jończyk, A.; Nawrot, Ewelina; Kisielewski, Michał

doi:10.1016/j.jfluchem.2005.09.013

Cited by 36 publications

(13 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nonfluorinated aliphatic alcohols remain problematic substrates for difluoromethylation and often give rise to low yields 218. Likewise, nitrogenous nucleophiles such as azoles,219 2‐mercaptoazoles,220 sulfonamides,221 sulfanyltetrazoles,222 benzotriazoles and tetrazoles,223 2‐acetaminopyridine,224 and indazoles225 can be converted into N ‐difluoromethylated products. Historically, other reagents used in N ‐difluoromethylations include Zn(CF 3 )Br,226 Cd(CF 3 ) 2 ,226a,b,d, 227 and Bi(CF 3 ) 3 /AlCl 3 ,226d all of which react through difluorocarbene intermediates.…”

Section: Difluoromethylationmentioning

confidence: 99%

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Liang¹,

Neumann²,

Ritter³

2013

Angew Chem Int Ed

2,303

856

View full text Add to dashboard Cite

Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo‐ and transition‐metal catalysis. The most challenging transformation remains the formation of the parent CF bond, primarily as a consequence of the high hydration energy of fluoride, strong metal—fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost‐efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.

show abstract

Section: Difluoromethylationmentioning

confidence: 99%

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Liang¹,

Neumann²,

Ritter³

2013

Angew Chem Int Ed

2,303

856

View full text Add to dashboard Cite

show abstract

“…as fluoroalkyl synthons for the synthesis of different fluorinecontaining compounds is of special interest. Such simple fluorine-containing substituents containing other halogen atoms besides fluorine can be transformed to more complex groups [1][2][3][4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Polyfluoroalkylation of 2,6-di-tert-butylphenol by 1,2-dibromotetrafluoroethane activated by sulfur dioxide

Koshechko

Kiprianova

Fileleeva

et al. 2006

Journal of Fluorine Chemistry

View full text Add to dashboard Cite

“…The synthesis of N-fl uoroalkyltetrazoles may be carried out also by the alkylation of the corresponding NH-unsubstituted tetrazoles. Jończyk et al showed that 5-benzyl-1H-tetrazole reacted with chlorodifl uoromethane in the presence of concentrated aqueous sodium hydroxide and a catalyst, benzyltriethylammonium chloride (TEBAC), in THF with the formation of regioisomeric N-difl uoromethyl substituted derivatives 104, 105 [ 98 ]. An interesting approach to the synthesis of tetrazoles with fl uorine atoms in the side chain was suggested by Fuchigami et al who performed an anodic monofl uorination of 1-substituted 5-tetrazolyl sulfi des containing an α-electronwithdrawing group (EWG) leading to the formation of the corresponding C-F derivatives 105 [ 99 ].…”

Section: Tetrazolesmentioning

confidence: 99%