84750-90-3Relevant academic research and scientific papers
Design and Synthesis of TY-Phos and Application in Palladium-Catalyzed Enantioselective Fluoroarylation of gem-Difluoroalkenes
Li, Zhiming,Lin, Tao-Yan,Liu, Yu,Pan, Zhangjin,Tu, Youshao,Wu, Hai-Hong,Zhang, Junliang,Zhu, Shuai
supporting information, p. 22957 - 22962 (2020/10/19)
The first example of highly enantioselective fluoroarylation of gem-difluoroalkenes with aryl halides is presented by using a new chiral sulfinamide phosphine (Sadphos) type ligand TY-Phos. N-Me-TY-Phos can be easily synthesized on a gram scale from readily available starting materials in three steps. Salient features of this work including readily available starting materials, good yields, high enantioselectivities as well as broad substrate scope make this approach very practical and attractive. Notably, the asymmetric synthesis of an analogue of a biologically active molecule is also reported.
Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes
Liu, Haidong,Ge, Liang,Wang, Ding-Xing,Chen, Nan,Feng, Chao
supporting information, p. 3918 - 3922 (2019/02/19)
A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.
Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes
Ma, Yu,Reddy, Bhoomireddy Rajendra Prasad,Bi, Xihe
supporting information, p. 9860 - 9863 (2019/12/24)
The synthesis of alkyl gem-difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.
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.
Copper-Catalyzed Regioselective Monodefluoroborylation of Polyfluoroalkenes en Route to Diverse Fluoroalkenes
Sakaguchi, Hironobu,Uetake, Yuta,Ohashi, Masato,Niwa, Takashi,Ogoshi, Sensuke,Hosoya, Takamitsu
supporting information, p. 12855 - 12862 (2017/09/25)
Monodefluoroborylation of polyfluoroalkenes has been achieved in a regioselective manner under mild conditions via copper catalysis. The method has shown an extremely broad scope of substrates, including (difluorovinyl)arenes, tetrafluoroethylene (TFE), (
Palladium-Catalyzed Fluoroarylation of gem-Difluoroalkenes
Tang, Hai-Jun,Lin, Ling-Zhi,Feng, Chao,Loh, Teck-Peng
supporting information, p. 9872 - 9876 (2017/08/08)
A Pd-catalyzed fluoroarylation of gem-difluoroalkenes with aryl halides is reported. By taking advantage of the in situ generated α-CF3-benzylsilver intermediates derived from the nucleophilic addition of silver fluoride to gem-difluoroalkenes, this strategy bypasses the use of a strong base, thus enabling a mild and general synthetic method for ready access to non-symmetric α,α-disubstituted trifluoroethane derivatives.
Visible light photocatalytic decarboxylative monofluoroalkenylation of α-amino acids with: Gem -difluoroalkenes
Li, Jingjing,Lefebvre, Quentin,Yang, Haijun,Zhao, Yufen,Fu, Hua
supporting information, p. 10299 - 10302 (2017/09/25)
α-Amino acids are among the most common biologically active molecules in nature, and their functionalization has attracted much attention. In this communication, a novel, efficient and general visible-light photocatalytic decarboxylative monofluoroalkenylation of N-protected α-amino acids with gem-difluoroalkenes is reported, affording the corresponding α-amino monofluoroalkenes which might find applications in medical chemistry and materials science. The reaction proceeded at room temperature with high efficiency and tolerance of various functional groups.
Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins
Zhang, Zhikun,Yu, Weizhi,Wu, Chenggui,Wang, Chengpeng,Zhang, Yan,Wang, Jianbo
supporting information, p. 273 - 277 (2016/01/25)
A transition-metal-free difluoromethylenation of diazo compounds that proceeds under mild conditions has been developed and is based on the use of TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the promoter. T
One-pot synthesis of gem-difluorostyrenes from benzyl bromide via olefination of phosphonium ylide with difluorocarbene
Deng, Xiao-Yun,Lin, Jin-Hong,Xiao, Ji-Chang
, p. 116 - 120 (2015/11/10)
A new approach for the synthesis of gem-difluorostyrenes from benzyl bromide is described. Quaternization of triphenylphosphine with benzyl bromide to give phosphonium salts, deprotonation of the corresponding phosphonium salts to produce phosphonium ylide, and the subsequent olefination of phosphonium ylide with difluorocarbene generated from difluoromethylene phosphobetaine (Ph3P+CF2CO2-) by decarboxylation can occur smoothly in one-pot, furnishing the final gem-difluorostyrenes in good yields.
Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources
Aikawa, Kohsuke,Toya, Wataru,Nakamura, Yuzo,Mikami, Koichi
supporting information, p. 4996 - 4999 (2015/11/03)
The trifluoromethylation of carbonyl compounds is accomplished by the stable (trifluoromethyl)zinc reagent generated and then isolated from CF3I and ZnEt2, which can be utilized as a trifluoromethyl anion source (CF3-). The reaction proceeds smoothly with diamine as a ligand and ammonium salt as an initiator, providing the corresponding trifluoromethylated alcohol products. Moreover, the (trifluoromethyl)zinc reagent can also be employed as a difluorocarbene source (:CF2) not only for gem-difluoroolefination of carbonyl compounds with phosphine but also for gem-difluorocyclization of alkenes or alkynes via the thermal decomposition, respectively.
