28321-12-2Relevant academic research and scientific papers
Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes with lithium organoborates
Huang, Weichen,Shen, Qilong,Xiao, Yisa
supporting information, (2022/02/02)
A method for stereoselective construction of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes in mild conditions was described. The combination of lithium organoborate and ZnBr2 generated in situ lithium ar
-Annulation of gem-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines
Zhang, Jun-Qi,Hu, Dandan,Song, Jinyu,Ren, Hongjun
, p. 4646 - 4660 (2021/04/06)
A [3 + 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing ambient air as the sole oxidant in an open-vessel manner, affording a series of multifunctionalized 2-fluoroindolizines in moderate to good yields. In this reaction, gem-difluoroalkene acts as a C2 synthon and entirely avoids the competitive addition-elimination process, which provides facile access to 2-fluoroindolizines.
Ni-Catalyzed Defluorination for the Synthesis of gem-Difluoro-1,3-dienes and Their [4 + 2] Cycloaddition Reaction
Zhou, Minqi,Zhang, Jian,Zhang, Xing-Guo,Zhang, Xingang
, p. 671 - 674 (2019/01/21)
A nickel-catalyzed defluorination of α-trifluoromethylated allyl/propargyl carbonates using bis(pinacolato)diboron (B2pin2) as a reactant is described. The reaction proceeds under relatively mild reaction conditions, providing conjug
Zinc-Mediated Decarboxylative Alkylation of Gem-difluoroalkenes
Yu, Liting,Tang, Mei-Lin,Si, Chang-Mei,Meng, Zhi,Liang, Yongxi,Han, Jilai,Sun, Xun
supporting information, p. 4579 - 4583 (2018/08/09)
An efficient and mild zinc-mediated decarboxylative alkylation of gem-difluoroalkenes with N-hydroxyphthalimide (NHP) esters, to give monofluoroalkenes in moderate to excellent yields with high Z-selectivity is reported. The reaction tolerates a broad range of functional groups and can be easily scaled up, which thus may pave the way for its further applications in medicinal chemistry and materials science.
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), (
Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water
Hu, Jiefeng,Han, Xiaowei,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 13342 - 13346 (2017/10/17)
A copper catalytic system was established for the stereoselective hydrodefluorination of gem-difluoroalkenes through C?F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good-functional group compatibility, accepting a range of carbonyls as precursors to the gem-difluoroalkenes, including aliphatic, aromatic, and α,β-unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late-stage modification of complex compounds.
Direct Difluoromethylenation of Carbonyl Compounds by Using TMSCF3: The Right Conditions
Krishnamoorthy, Sankarganesh,Kothandaraman, Jotheeswari,Saldana, Jacqueline,Prakash, G. K. Surya
supporting information, p. 4965 - 4969 (2016/10/26)
A deoxygenative difluoromethylenation of carbonyl compounds has been developed by using readily available, inexpensive trifluoromethyltrimethylsilane, LiI, and PPh3. The presence of the Li+ion prevents the unproductive exhaustion of trifluoromethyltrimethylsilane (TMSCF3) by keeping the soluble free fluoride concentration in the reaction medium under control. The strategy of combining solvents to increase the reactivity and thereby reduce the reaction temperature and time is disclosed.
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.
Decarboxylative Julia-Kocienski gem-Difluoro-Olefination of 2-Pyridinyl Sulfonyldifluoroacetate
Wang, Xiao-Ping,Lin, Jin-Hong,Xiao, Ji-Chang,Zheng, Xing
, p. 928 - 932 (2015/10/05)
The decarboxylation of potassium 2-pyridinyl sulfonyldifluoroacetate and its subsequent reaction with aldehydes was found to be an efficient approach for the Julia-Kocienski reaction under mild conditions to give gem-difluoro olefins in moderate to excellent yields. Owing to its high stability in the pure state and its easy decarboxylation in polar solvents, potassium 2-pyridinyl sulfonyldifluoroacetate is expected to be an efficient gem-difluoro-olefination reagent. The decarboxylation of potassium 2-pyridinyl sulfonyldifluoroacetate and its subsequent reaction with aldehydes is an efficient approach for the Julia-Kocienski reaction under mild conditions to give gem-difluoro olefins in moderate to excellent yields.
Wittig gem-difluoroolefination of aldehydes with difluoromethyltriphenylphosphonium bromide
Li, Qiang,Lin, Jin-Hong,Deng, Zu-Yong,Zheng, Jian,Cai, Ji,Xiao, Ji-Chang
, p. 38 - 41 (2014/06/09)
Wittig reaction of aldehydes with difluoromethyltriphenylphosphonium bromide leading to gem-difluoroolefins in moderate yields is described. The reaction displays a good substrate scope including aryl, heteroaryl and α,β-unsaturated aldehydes. Difluoromethyltriphenylphosphonium bromide could be easily prepared and stored for a long time under air atmosphere. The salt exhibits high thermal stability demonstrated by thermogravimetric analysis. Its structure was confirmed by NMR spectroscopy and single crystal X-ray analysis.
