26351-62-2Relevant academic research and scientific papers
Reactions of alkali metal macrocyclic complexes XIX. Reaction of potassium or sodium complexes with oxetane - novel route to organometallic compounds
Jedlinski, Zbigniew,Misiolek, Andrzej,Jankowski, Andrzej,Janeczek, Henryk
, p. 231 - 239 (1992)
Novel reactions of oxetane with K-/K+ and Na-/K+ complexes in which potassium cation is complexed by 18-crown-6 have been studied.Organometallic alkoxides formed by cleavage of an alkyl-oxygen bond in the oxetane molecule were used for one pot metallation of anisole and triphenylmethane.The reaction with carbon dioxide was also investigated.Reaction mechanisms have been studied by NMR, GLC-MS, IR techniques and chemical analysis.
Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides
Bartling, Stephan,Beller, Matthias,Bourriquen, Florian,Junge, Kathrin,Li, Wu,Liu, Weiping,Qu, Ruiyang,Rockstroh, Nils
, p. 14033 - 14038 (2021/11/12)
The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification of metabolites. Hence, methodologies for the synthesis of selectively labelled compounds continue to be a major area of interest for many scientists. Herein, we present a practical and stable heterogeneous copper catalyst, which permits for dehalogenative deuterationviawater-gas shift reaction at comparably low temperature. This novel approach allows deuteration of diverse (hetero)aryl halides with good functional group tolerance, and no reduction of the aromatic rings or other easily reducible formyl and cyano groups. Multi-gram experiments show the potential of this method in organic synthesis and medicinal chemistry.
Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
supporting information, p. 1297 - 1300 (2020/12/23)
A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
Preparation of Thioanisole Biscarbanion and C-H Lithiation/Annulation Reactions for the Access of Five-Membered Heterocycles
Zhu, Ranran,Liu, Zheyuan,Chen, Jie,Xiong, Xiaoyu,Wang, Yuntao,Huang, Lin,Bai, Jinshan,Dang, Yanfeng,Huang, Jianhui
supporting information, p. 3161 - 3165 (2018/06/11)
The synthesis, isolation, and X-ray structure of a thioanisole-based trilithium complex are reported. On the basis of the double-lithiation strategy, two novel synthetic methodologies have been developed under mild reaction conditions (room temperature): (1) reactions of lithiated thioanisoles with nitriles give benzoisothiazoles via a [3 + 2]-type of approach with two new bond formations and (2) formation of benzothiophenes from thioanisoles and amides through a [4 + 1] pattern forming 4 new chemical bonds.
Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Arene Metalations
Algera, Russell F.,Ma, Yun,Collum, David B.
supporting information, p. 15197 - 15204 (2017/10/31)
Sodium diisopropylamide (NaDA)-mediated metalations of arenes in tetrahydrofuran (THF)/hexane or THF/Me2NEt solutions are described. A survey of >40 benzenoid- and pyridine-based arenes with a range of substituents demonstrates the efficacy and regioselectivity of metalation. Metalations of activated disubstituted arenes and selected monosubstituted arenes are rapid at -78 °C. Rate studies of 1,3-dimethoxybenzene and related methoxylated arenes show exclusively monomer-based orthometalations with two or three coordinated THF ligands. Rate studies of the isotopic exchange of benzene and monosubstituted arenes with weakly activating groups reveal analogous di- and trisolvated monomer-based metalations. Cooperative inductive, mesomeric, steric, and chelate effects are discussed.
Regio- and chemoselective direct generation of functionalized aromatic aluminum compounds using aluminum ate base
Uchiyama, Masanobu,Naka, Hiroshi,Matsumoto, Yotaro,Ohwada, Tomohiko
, p. 10526 - 10527 (2007/10/03)
A regio- and chemoselective direct method for generation of functionalized aromatic aluminum compounds through deprotonative directed ortho-alumination using triisobutyl(tetramethylpiperidino)aluminate (iBu3Al(TMP)Li), prepared by mixing of triisobutylaluminum (iBu3Al) and lithium tetramethylpiperidide (LTMP) in THF, has been developed. Deprotonative alumination of various functionalized benzenes with the use of iBu3Al(TMP)Li proved effective for the direct generation of various ortho-functionalized aluminum aromatic and heteroaromatic derivatives, particularly those with electrophilic functional groups such as cyano, amide, and halogen. Direct alumination, followed by electrophilic trapping (with I2), provided a convenient preparative method for 1,2- or 1,2,3-multisubstituted aromatic compounds. The functionalized aromatic aluminate intermediate also was found to undergo copper- and palladium-catalyzed C-C bond-forming reactions very efficiently and highly regio- and chemoselectively. Copyright
