21486-48-6Relevant academic research and scientific papers
Selective Fluoromethyl Couplings of Alkynes via Nickel Catalysis
Li, Huan,Wang, Fang,Zhu, Shengqing,Chu, Lingling
supporting information, (2022/01/20)
We describe here a Ni-catalyzed intermolecular carbo-fluoromethylation of alkynes with aliphatic halides and fluoromethyl halides (BrCF2H and ICH2F) in the presence of zinc, enabling the facile and selective access to a diverse range of biologically valuable CF2H/CH2F-incorporated alkenes with excellent regio- and stereoselectivity. Notably, merging intramolecular radical cyclization with fluoromethyl coupling enables the expedient constructions of CF2H/CH2F-incorporated lactones and lactams with high efficiency and selectivity. Mechanistic studies disclose that this catalytic protocol proceeds via a radical addition to an alkyne followed by selective coupling with the fluoromethyl unit.
Optimization of bifunctional piperidinamide derivatives as σ1R Antagonists/MOR agonists for treating neuropathic pain
Chen, Yin,Hao, Chao,Liu, Bi-Feng,Liu, Xin,Ma, Ru,Ma, Yurong,Xiong, Jiaying,Xu, Junyi,Ye, Jiaqi,Zhang, Guisen,Zhang, Shuang,Zhuang, Tao
, (2021/10/12)
Here, we describe the optimization, synthesis, and associated pharmacological analgesic activities of a new series of bifunctional piperidinamide derivatives as sigma-1 receptor (σ1R) antagonists and mu opioid receptor (MOR) agonists. The new compounds were evaluated in vitro in σ1R and MOR binding assays. The most promising compound 114 (also called HKC-126), showed superior affinities for σ1R and MOR and good selectivity to additional receptors related to pain. Compound 114 showed powerful dose-dependent analgesic effects in the acetic acid writhing test, formalin test, hot plate test, and chronic constriction injury (CCI) neuropathic pain model. In contrast to an equianalgesic dose of fentanyl, compound 114 produced fewer opioid-like side effects, such as reward liability, respiratory depression, physical dependence, and sedation. Lastly, the pharmacokinetic properties of this drug were also acceptable, and these results suggest that compound 114, as a mixed σ1R/MOR ligand, has potential for treating neuropathic pain.
Transition-Metal-Free Coupling of Alkynes with α-Bromo Carbonyl Compounds: An Efficient Approach towards β,γ-Alkynoates and Allenoates
Liu, Wenbo,Chen, Zhengwang,Li, Lu,Wang, Haining,Li, Chao-Jun
supporting information, p. 5888 - 5893 (2016/04/26)
A direct transition-metal-free coupling between alkynes and α-bromo carbonyl compounds has been developed with ultraviolet (UV) light in aqueous media. This method represents a facile approach to synthetically useful β,γ-alkynyl esters and amides stereoselectively from two readily available starting materials. As an example of the synthetic application of the products, the alkynyl esters were readily converted into allenoates. Time for UV! A direct coupling between alkynes and α-bromo compounds has been developed with ultraviolet light in aqueous media (see scheme). This method represents a facile approach to synthetically useful β,γ-alkynyl esters and amides stereoselectively from two readily available starting materials.
New directing groups for metal-catalyzed asymmetric carbon-carbon bond-forming processes: Stereoconvergent alkyl-alkyl suzuki cross-couplings of unactivated electrophiles
Wilsily, Ashraf,Tramutola, Francesco,Owston, Nathan A.,Fu, Gregory C.
supporting information; experimental part, p. 5794 - 5797 (2012/05/07)
The ability of two common protected forms of amines (carbamates and sulfonamides) to serve as directing groups in Ni-catalyzed Suzuki reactions has been exploited in the development of catalytic asymmetric methods for cross-coupling unactivated alkyl electrophiles. Racemic secondary bromides and chlorides undergo C-C bond formation in a stereoconvergent process in good ee at room temperature in the presence of a commercially available Ni complex and chiral ligand. Structure-enantioselectivity studies designed to elucidate the site of binding to Ni (the oxygen of the carbamate and of the sulfonamide) led to the discovery that sulfones also serve as useful directing groups for asymmetric Suzuki cross-couplings of racemic alkyl halides. To our knowledge, this investigation provides the first examples of the use of sulfonamides or sulfones as effective directing groups in metal-catalyzed asymmetric C-C bond-forming reactions. A mechanistic study established that transmetalation occurs with retention of stereochemistry and that the resulting Ni-C bond does not undergo homolysis in subsequent stages of the catalytic cycle.
Anilide herbicides
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, (2008/06/13)
A novel herbicide of formula I STR1 wherein R1 represents a halogen atom or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group; R2 represents a hydrogen or halogen atom; each of R3 to R6 independently represents a hydrogen or halogen atom or a cyano, alkyl, haloalkyl, alkoxy or haloalkoxy group; R7 represents a hydrogen or halogen atom, or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group; and A represents a nitrogen atom or a --CH-- group, together with its formulation and use as a herbicide, and its preparation.
