131323-06-3Relevant articles and documents
Aromatic substitution with photochemically generated difluoromethyl radicals bearing electron-withdrawing group
Murakami, Satoru,Kim, Shokaku,Ishii, Hideki,Fuchigami, Toshio
, p. 815 - 818 (2004)
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.
Synthesis of α-Fluorinated Areneacetates through Photoredox/Copper Dual Catalysis
Levitre, Guillaume,Granados, Albert,Cabrera-Afonso, María Jesús,Molander, Gary A.
supporting information, p. 3194 - 3198 (2022/05/11)
The development of mild and practical conditions for the fluoroalkylation of arenes is an ongoing challenge in chemical organic synthesis. Herein, we report a metallaphotoredox method for the preparation of fluoroalkyl arenes based on the synergistic combination of Ir/Cu dual catalysis from boronic acids. The mild conditions allow broad functional group tolerance, including substrates containing aldehydes, free phenols, and N-Boc-protected amines. Mechanistic investigations support a process proceeding via photoredox/copper dual catalysis.
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.
Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C-H/N-H Coupling
Zhang, Lanfei,Zhang, Xiaofei,Cui, Yongmei,Yang, Chunhao
supporting information, p. 3815 - 3826 (2021/06/28)
Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenyl ethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C-H/N-H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.
Cobalt-Catalyzed α-Arylation of Substituted α-Bromo α-Fluoro β-Lactams with Diaryl Zinc Reagents: Generalization to Functionalized Bromo Derivatives
Br?se, Stefan,Chen, Hi-Yung,Cossy, Janine,Koch, Vanessa,Lei, Aiwen,Lorion, Mélanie M.,Nieger, Martin
supporting information, p. 13163 - 13169 (2020/09/23)
A cobalt-catalyzed cross-coupling of α-bromo α-fluoro β-lactams with diarylzinc or diallylzinc reagents is herein disclosed. The protocol proved to be general, chemoselective and operationally simple allowing the C4 functionalization of β-lactams. The substrate scope was expanded to α-bromo lactams and amides, α-bromo lactones and esters as well as N- and O-containing heterocycles.
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
Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination
Shao, Changdong,Shi, Guangfa,Zhang, Yanghui
, p. 5529 - 5538 (2016/11/25)
An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.
PYRROLOPYRIMIDINE DERIVATIVES AS NR2B NMDA RECEPTOR ANTAGONISTS
-
Paragraph 0375, (2016/04/09)
Disclosed are chemical entities of formula I: [INSERT CHEMICAL FORMULA HERE] wherein X, Y, Z, R1, R3, R4, R5 and R6 are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of formula I, and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of formula I.
Silver-catalyzed oxidative decarboxylation of difluoroacetates: Efficient access to C-CF2 bond formation
Wan, Wen,Ma, Guobin,Li, Jialiang,Chen, Yunrong,Hu, Qingyang,Li, Minjie,Jiang, Haizhen,Deng, Hongmei,Hao, Jian
, p. 1598 - 1601 (2016/01/30)
A mild, versatile and efficient method for the silver(i)-catalyzed oxidative decarboxylative gem-difluoromethylenation has been developed. The radical cascade reaction comprises the addition of an oxidatively generated difluoromethylene radical to the isonitrile functionality and subsequent homolytic aromatic substitution. It provides a novel and efficient access to the C-CF2 bond formation.
Cobalt-catalyzed cross-coupling reaction of arylzinc reagents with ethyl bromodifluoroacetate
Araki, Keisuke,Inoue, Munenori
, p. 3913 - 3918 (2013/06/27)
Transition metal-catalyzed cross-coupling reactions of arylmetal reagents with ethyl bromodifluoroacetate have been explored. After intensive investigations, we have successfully found that a cobalt-catalyzed cross-coupling reaction (catalytic alkoxycarbonyldifluoromethylation) of arylzinc reagents with ethyl bromodifluoroacetate smoothly proceeded to afford the corresponding ethyl aryldifluoroacetates in moderate to good yields.
