38841-95-1Relevant academic research and scientific papers
Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
Li, Zijian,Sun, Wenxuan,Wang, Xianxu,Li, Luyang,Zhang, Yong,Li, Chao
supporting information, p. 3536 - 3543 (2021/03/08)
As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.
Remote migratory cross-electrophile coupling and olefin hydroarylation reactions enabled by in situ generation of nih
Chen, Fenglin,Chen, Ke,Zhang, Yao,He, Yuli,Wang, Yi-Ming,Zhu, Shaolin
supporting information, p. 13929 - 13935 (2017/11/07)
A highly efficient strategy for remote reductive cross-electrophile coupling has been developed through the ligand-controlled nickel migration/arylation. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1, 1-diarylalkanes in excellent yields and high regioselectivities under mild conditions. We also demonstrated that alkyl bromide could be replaced by the proposed olefin intermediate while using n-propyl bromide/Mn0 as a potential hydride source.
Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling
Dupuy, Stéphanie,Zhang, Ke-Feng,Goutierre, Anne-Sophie,Baudoin, Olivier
supporting information, p. 14793 - 14797 (2016/11/23)
Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C?H bond functionalization methods. We describe herein a new step-economical approach that enables C?C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
Hole transfer promoted hydrogenation: One-electron oxidation as a strategy for selective reduction of π-bonds
Mirafzal, Gholam A.,Liu, Jianping,Bauld, Nathan L.
, p. 6072 - 6077 (2007/10/02)
One-electron oxidation is developed as a strategy for selective and efficient reduction of relatively ionizable functionalities, including conjugated dienes, styrenes, vinyl sulfides, aromatics, and even strained σ-bonds. Reduction is highly sensitive to substrate ionizability and permits selective reduction of the more ionizable function in a difunctional context. Ionization of the substrates to cation radicals is effected via the mild hole transfer agent tris(4-bromophenyl)aminium hexachloroantimonate, and subsequent reduction of the cation radicals is accomplished by tributyltin hydride. The new reduction conditions provide a novel route for generating free radicals which may prove useful in the field of radical cyclizations. This is especially attractive in the case of phenyl vinyl sulfides since the phenylthio group, which remains intact subsequent to cyclization, provides versatile functionality for further synthetic operations.
Synthesis and Hypolipidemic Activity of 2-Substituted Isobutyric Acid Derivatives
Morishita, Shin-ichi,Saito, Takashi,Hirai, Yasuharu,Shoji, Masamichi,Mishima, Yasuhiro,Kawakami, Masato
, p. 1205 - 1209 (2007/10/02)
A series of 2-substituted isobutyric acid derivatives have been synthesized and evaluated as hypolipidemic agents.Compounds 11 and 20 were found to decrease the level of plasma total cholesterol in experimental hyperlipidemic rats to a greater extent than clofibrate (CF) and to increase the level of plasma high-density lipoprotein cholesterol to the same extent as gemfibrozil (GF).Increase in liver weight caused by these compounds were less than those with CF and GF.
