73790-00-8Relevant academic research and scientific papers
Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds
Wang, Pingyang,Du, Pengcheng,Sun, Qianqian,Zhang, Jianhua,Deng, Hongmei,Jiang, Haizhen
supporting information, p. 2023 - 2029 (2021/03/16)
An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.
Visible Light-Promoted Phosphine-Catalyzed Difluoroalkylation of Arenes and Heterocycles
Lu, Heng,Wang, Dong-Yu,Zhang, Ao
, p. 942 - 951 (2020/02/04)
A visible light-promoted difluoroalkylation reaction of arenes or heterocycles, using triaryl phosphine as the catalyst and difluoroalkyl iodide as the alkylating agent, is presented. The strategy is highlighted by photocatalyst-free, mild reaction conditions and a broad substrate scope. Mechanistic experiments indicate that this reaction involves a radical-chain process that is initiated by an electron donor-acceptor complex formed from difluoroalkyl iodide and phosphine.
Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of α,α-Difluoroarylacetic Acids with Acrylamides To Synthesize Difluorinated Oxindoles
Li, Yin-Long,Wang, Ji-Bo,Wang, Xue-Lin,Cao, Yang,Deng, Jun
supporting information, p. 6052 - 6059 (2017/11/14)
A facile silver-catalyzed decarboxylative radical addition/cyclization reaction of α,α-difluoroarylacetic acids and acrylamides has been disclosed. The method provides a highly attractive approach to synthesize a series of difluorinated oxindoles that contain various functional groups in moderate to good yields under mild conditions. Moreover, experimental studies reveal that the CF2 group of the α,α-difluoroarylacetic acids plays a vital role in the transformation.
Silver-Mediated C–H Difluoromethylation of Arenes
Li, Jialiang,Wan, Wen,Ma, Guobin,Chen, Yunrong,Hu, Qingyang,Kang, Kai,Jiang, Haizhen,Hao, Jian
supporting information, p. 4916 - 4921 (2016/10/13)
The first AgI-mediated C–H ethoxycarbonyl difluoromethylation with TMSCF2COOEt (TMS = trimethylsilyl) has been developed. The radical difluoromethylation proceeds smoothly to give the difluoromethylated arenes in moderate to high yie
Copper-mediated aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides at room temperature
Qi, Qingqing,Shen, Qilong,Lu, Long
supporting information; experimental part, p. 6548 - 6551 (2012/06/04)
A Cu-mediated ligandless aerobic fluoroalkylation of arylboronic acids under mild conditions is described for the first time. The reaction tolerates a wide range of functional groups, allowing for further transformation. Mechanistic studies suggest that [RfCu] is the active Cu species that forms the desired perfluoroalkylarenes and that [RfCu] is generated from [PhCu] by either an oxidative addition/reductive elimination mechanism or nucleophilic substitution via a halogen "ate" intermediate.
Desulfurizing difluorination reaction of benzyl sulfides using IF 5
Fukuhara, Tadahito,Hara, Shoji
scheme or table, p. 198 - 200 (2009/05/30)
A desulfurizing difluorination reaction of benzyl sulfides having a functional group such as an ester, a ketone, a nitrile, or an amide was performed by a reaction with IF5. Consequently, gemdifluoro compounds could be obtained selectively. Geo
Aromatic substitution with photochemically generated difluoromethyl radicals bearing electron-withdrawing group
Murakami, Satoru,Kim, Shokaku,Ishii, Hideki,Fuchigami, Toshio
, p. 815 - 818 (2007/10/03)
Novel and facile aromatic and heteroaromatic substitutions with difluoromethyl radicals bearing electron-withdrawing group generated by the photo-initiated Se-CF2 bond cleavage of ethyl α,α- difluoro-α-(phenylseleno)acetate and diethyl α,α- difluoromethyl-α-(phenylseleno)phosphonate were successfully carried out to provide the corresponding α-aryl-α,α-difluoroacetates and a-aryl-α,α-difluoromethylphosphonates in good to moderate yields.
&α,&α-Difluoroarylacetic Acids: Preparation from (Diethylamino)sulfur Trifluoride and &α-Oxoarylacetates
Middleton, W. J.,Bingham, E. M.
, p. 2883 - 2887 (2007/10/02)
Several α,α-difluoroarylacetic acids have been prepared by reaction of DAST ((diethylamino)sulfur trifluoride) with esters of α-oxoarylacetic acids and then hydrolysis of the resulting difluoro ester.Examples include the α,α-difluoro derivates of the synthetic plant auxin, α-naphthylacetic acid, and the antiinflammatory drug, ibufenac.
