1022094-52-5Relevant articles and documents
Synthesis of alkyl aryl(heteroaryl)acetates from N-oxides, 1,1-difluorostyrenes, and alcohols
Loska, Rafal,Szachowicz, Katarzyna,Szydlik, Dorota
, p. 5706 - 5709 (2013)
Derivatives of aryl(heteroaryl)acetic acids or aryl(heteroaryl)methanes are formed from imidazole or thiazole N-oxide, 1,1-difluorostyrene, and an alcohol, amine, or water in a three-component reaction, which probably occurs via 1,3-dipolar cycloaddition.
Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes
Song, Shengjin,Liu, Huan,Wang, Lu,Zhu, Chuan,Loh, Teck-Peng,Feng, Chao
, p. 1036 - 1040 (2019)
Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.
A one-step synthesis of gem-difluoroolefins from alcohols
Gu, Jinying,Lin, Jin-Hong,Tang, Ting,Xiao, Can,Xiao, Ji-Chang,Xiao, Xuan,Yao, Xu,Yu, Jiao,Zheng, Xing
, (2020)
The development of efficient protocols for the synthesis of gem-difluoroolefins has received increasing attention. Given the ubiquity of hydroxyl group in biologically active molecules and synthetic intermediates, we developed a one-step protocol for the conversions of alcohols into gem-difluoroolefins. The reactions of alcohols with Ph3P+CF2CO2?/Burgess reagent in DMSO occurred smoothly to afford the final products in moderate to high yields. DMSO is not only necessary for the oxidation process, but also important for the stabilization of phosphonium ylide by trapping difluorocarbene.
Autocatalytic Synthesis of Thioesters via Thiocarbonylation of gem-Difluoroalkenes
Jiang, Xinpeng,Wang, Guan,Zheng, Zicong,Yu, Xiaohui,Hong, Ye,Xia, Haoqi,Yu, Chuanming
, p. 9762 - 9766 (2020)
Herein, we report a new method for the synthesis of acyethanethioates via thiocarbonylation of gem-difluoroalkenes with thiols. This reaction provides a new pathway to prepare thioesters under mild conditions without the use of any additives. Mechanistic
Asymmetric Synthesis of 2,2-Difluorotetrahydrofurans through Palladium-Catalyzed Formal [3+2] Cycloaddition
Liu, Jun,Yu, Longhui,Zhao, Gang,Zheng, Changwu
supporting information, p. 23641 - 23645 (2021/10/05)
The asymmetric synthesis of 2,2-difluorinated tetrahydrofurans was accomplished via enantioselective formal [3+2] cycloaddition catalyzed by palladium. The asymmetric reaction between gem-difluoroalkenes and racemic vinyl epoxides or vinylethylene carbonates resulted in the formation of enantioenriched 2,2-difluorotetrahydrofurans with an enantioselectivity up to 98 %. Notably, the reaction used the readily available (R)-BINAP as the ligand at a low loading and yielded a wide variety of difluorinated products in moderate to high yields. Both chiral diastereomers could be obtained in a single sequence.
Highly E-Selective Synthesis of α-Fluoro-β-arylalkenyl Sulfones from gem-Difluoroalkenes with Sodium Sulfinates
Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
, p. 6983 - 6993 (2021/05/06)
The straightforward synthesis of α-fluoro-β-arylalkenyl sulfones under transition-metal-and base-free conditions has been described, which displays broad functional group compatibility and high stereoselectivity. In particular, the strategy is also applied to the late-stage modification of complex natural products and drugs.
