75633-89-5Relevant academic research and scientific papers
Nickel-Catalyzed Hydroalkenylation of Alkynes through C-F Bond Activation: Synthesis of 2-Fluoro-1,3-dienes
Watabe, Yota,Kanazawa, Kohei,Fujita, Takeshi,Ichikawa, Junji
, p. 3569 - 3575 (2017)
2-Fluoro-1,3-dienes were synthesized through nickel-catalyzed coupling reactions between β,β-difluorostyrenes and alkynes in the presence of ZrF 4 as co-catalyst and a hydride source derived from triethylborane and lithium isopropoxide. Mechanistic studies revealed that the carbon-fluorine bond was cleaved by β-fluorine elimination from intermediary nickelacyclopentenes generated through oxidative cyclization of the two substrates.
Dehalogenative Cross-Coupling of gem-Difluoroalkenes with Alkyl Halides via a Silyl Radical-Mediated Process
Tian, Hao,Yang, Shaoxiang,Wang, Xiaochen,Xu, Wentao,Liu, Yuxiu,Li, Yongqiang,Wang, Qingmin
supporting information, p. 12772 - 12782 (2021/09/13)
Herein, we describe a convenient general protocol for monofluoroalkenylation reactions of alkyl bromides involving cooperative visible-light photoredox catalysis and halogen abstraction. Mechanistic experiments showed that the products were generated by selective cross-coupling of aliphatic radicals with fluoroalkenyl radicals. Silyl radical-mediated halogen abstraction enabled the protocol to be used for the monofluoroalkenylation of a broad range of alkyl and heteroaryl halides. The protocol could be carried out on a gram scale and was applied to cholesterol, indicating its utility for late-stage monofluoroalkenylation reactions.
Metal-Free Access to (E/Z)-α-Fluorovinyl Phosphorus Compounds from gem-Difluorostyrenes
Peng, Yingyuan,Zhang, Xiaofei,Qi, Xueyu,He, Qian,Zhang, Bin,Hao, Jian,Yang, Chunhao
, p. 1170 - 1177 (2019/01/16)
A facile and efficient method for the synthesis of (E/Z)-α-fluorovinyl phosphorus compounds from gem-difluorostyrenes with diphenylphosphine oxide/dialkyl phosphate and DBU at room temperature was developed. A series of 1-fluorovinyl phosphine oxides/phosphonates were obtained with moderate to excellent yields in these reactions. Additionally, most isomers (E/Z type) of the target compounds could be easily separated and purified by column chromatography.
DEFLUORINATION REACTIONS OF gem-DIFLUORO- AND MONOFLUOROOLEFINS. NOVEL METHODS FOR ONE-CARBON HOMOLOGATIONS OF CARBONYL COMPOUNDS LEADING TO ALDEHYDES, CARBOXYLIC ACIDS, AND ESTERS
Hayashi, Sei-ichi,Nakai, Takeshi,Ishikawa, Nobuo
, p. 651 - 654 (2007/10/02)
Defluorinative hydrolysis (or alcoholysis) of gem-difluoroolefins (1) easily prepared via the facile difluoromethylenation of carbonyl compounds afforded the carboxylic acids (or esters).The homologation method was applied to the synthesis of anti-inflammatory ibuprofen.Furthermore, defluorinative hydrolysis of monofluoroolefins obtained via the reduction of 1 gave the aldehydes.
