110889-05-9Relevant academic research and scientific papers
Indium-mediated reaction of 3-bromo-3,3-difluoropropene and bromodifluoromethylacetylene derivatives with aldehydes
Kirihara, Masayuki,Takuwa, Tomofumi,Takizawa, Shinobu,Momose, Takefumi,Nemoto, Hideo
, p. 8275 - 8280 (2000)
Aldehydes reacted with 3-bromo-3,3-difluoropropene at the α-position in the presence of indium to afford 1-substituted-2,2-difluorobut-3-en-1-ols. Ketones and other electrophiles are inert under the examined conditions. The reaction of bromodifluoromethyl
gem-Difluoropropargylation of aldehydes using cat. In/Zn in aqueous media
Arimitsu, Satoru,Jacobsen, Jesse M.,Hammond, Gerald B.
, p. 1625 - 1627 (2007)
Zn (0.9 equiv) in combination with catalytic amounts of In (0.1 equiv) and I2 (0.1 equiv) was found to effect the reaction of several difluoropropargyl bromide derivatives with aldehydes to produce gem-difluorohomopropargyl alcohols in aqueous
Mg(0)-promoted debromometalation of gem-difluoropropargyl bromides
Mae, Masayuki,Hong, Jiyoung A.,Hammond, Gerald B.,Uneyama, Kenji
, p. 1787 - 1789 (2005)
Mg(0)/Me3SiCl was found to be effective for the preparation of difluoropropargylsilanes. This method, using Me3SnCl, produced the corresponding propargylstannane.
Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols
Hamel, Jean-Denys,Paquin, Jean-Fran?ois
, p. 11 - 23 (2018/10/20)
The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclizatio
Nucleophilic and electrophilic substitutions of difluoropropargyl bromides
Hammond, Gerald B.
, p. 476 - 488 (2008/03/14)
Fundamental organic reactions like nucleophilic and electrophilic substitutions have seldom been studied on fluorinated propargyl or allenyl modules, when the carbon atom undergoing substitution is bonded to two fluorine atoms. Herein we report a practical synthesis of difluoropropargyl bromides from substituted acetylenes and dibromodifluorometane using a wide variety of alkyl, aryl or silyl substrates. The synthesis of O-, S- and carboxylic acid derivatives of difluoropropargyl bromide is also described. These compounds are suitable starting materials for the synthesis of electrophilically substituted difluoropropargyl derivatives via magnesium and fluoride promoted reactions. An indium-mediated reaction of silyldifluoropropargyl bromide, followed by electrophilic trapping with bromine led to a very useful bromoallene, which was then used in reactions with nucleophiles (C, O, N, P, S, Hal) to yield a de facto bimolecular nucleophilic substitution of a difluoropropargyl bromide.
Lanthanide triflate-catalyzed preparation of β,β- difluorohomopropargyl alcohols in aqueous media. Application to the synthesis of 4,4-difluoroisochromans
Arimitsu, Satoru,Hammond, Gerald B.
, p. 8665 - 8668 (2007/10/03)
An indium-mediated Barbier-type reaction of difluoropropargyl bromide with several aldehydes in aqueous media was enhanced by a catalytic amount of a lanthanide triflate (5 mol %). The reaction gave the corresponding β,β-difluorohomopropargyl alcohols wit
A New and Concise Synthesis of 3-Fluoro-2,5-disubstituted Furans
Sham, Hing L.,Betebenner, David A.
, p. 1134 - 1135 (2007/10/02)
A highly efficient synthesis of a series of 3-fluoro-2,5-disubstituted furans by a two-step sequence is described.
THE REFORMATSKY REACTION OF BROMODIFLUOROMETHYLACETYLENE DERIVATIVES: APPLICATION TO THE SYNTHESIS OF FLUORINATED BIOACTIVE COMPOUNDS
Hanzawa, Yuji,Inazawa, Kazuhiko,Kon, Akira,Aoki, Hironobu,Kobayashi, Yoshiro
, p. 659 - 662 (2007/10/02)
The Reformatsky reaction of bromodifluoromethylacetylene derivatives with aldehydes gave fluorinated homopropargylic alcohols.The adducts obtained from D-glyceraldehyde acetonide were converted to 2,2-difluoro-2-deoxy-D-ribose and intermediates to fluorinated arachidonic acid and its metabolite.
