372492-47-2Relevant articles and documents
Deuterium exchange mediated by an iridium-phosphine complex formed in situ
Ellames, George J,Gibson, Jennifer S,Herbert, John M,Kerr, William J,McNeill, Alan H
, p. 6413 - 6416 (2001)
Bis(triorganophosphine)(cyclooctadiene)iridium(I) tetrafluoroborates, 2, are readily generated in situ and utilised for the exchange of deuterium into a variety of aromatic substrates. The efficiencies of deuterium exchange using 2 formed in this way are comparable to those observed in exchange processes where the isolated pre-catalysts were used.
A solid-phase iridium-based ortho-exchange catalyst for the one-step labelling of aromatic substrates with deuterium
Hickey, Michael J.,Jones, John R.,Kingston, Lee P.,Lockley, William J.S.,Mather, Andrew N.,Wilkinson, David J.
, p. 8621 - 8623 (2004)
A wide range of aromatic compounds containing suitable directing groups can be labelled efficiently with deuterium using isotopic exchange catalysed by an easily prepared polystyrene based ortho-exchange catalyst. The labelling reactions can be carried out efficiently at ambient temperature by simple stirring of the substrate and catalyst under a deuterium atmosphere for a few hours. Isolation consists of a simple filtration and evaporation of the solvent. Deuterium is incorporated with ortho-regiospecificity.
Electrochemically enabled rhodium-catalyzed [4 + 2] annulations of arenes with alkynes
Chen, Jia-Yi,Li, Ming,Li, Rui-Tao,Ma, Qiang,Ni, Shao-Fei,Wang, Zi-Chen,Wen, Li-Rong,Zhang, Lin-Bao
supporting information, p. 9515 - 9522 (2021/12/09)
Herein, electrochemically driven, Rh(iii)-catalyzed regioselective annulations of arenes with alkynes have been established. The strategy, combining the use of a rhodium catalyst with electricity, not only avoids the need for using a stoichiometric amount of external oxidant, but also ensures that the transformations proceed under mild and green conditions, which enable broad functional group compatibility with a variety of substrates, including drugs and pharmaceutical motifs. Moreover, the electrolysis reaction was made operationally simple by employing an undivided cell, and proceeds efficiently in aqueous solution in air. This journal is
A mechanistic study of transfer hydrogenation catalyzed by cyclometallated ruthenium half-sandwich complexes
Din Reshi, Noor U.,Senthurpandi, Dineshchakravarthy,Samuelson, Ashoka G.
, p. 189 - 199 (2018/05/04)
Transfer hydrogenation of aromatic ketones catalyzed by eight cyclometallated ruthenium half-sandwich complexes, including three new complexes, was examined. The catalytic process was studied using different ratios of substrate to base and base to catalyst and using a deuterated reductant. Optimum conditions for catalysis were shown to be in the presence of higher amounts of base in refluxing isopropanol. Under these conditions, the complexes were reduced in situ to give Ru(0) nanoparticles invisible to the naked eye. The nanoparticles were characterized by TEM, DLS and XPS. The catalytic transfer hydrogenation, under conditions in which nanoparticles were generated, was found to be far greater than the transfer hydrogenation by the molecular catalyst. Complete characterization of the three new complexes, including the X-ray crystallographic characterization of these complexes was carried out.
Palladium-Catalyzed Trifluoromethylthiolation of Chelation-Assisted C–H Bonds
Kesavan, Arunachalam,Chaitanya, Manthena,Anbarasan, Pazhamalai
, p. 3276 - 3279 (2018/07/13)
An efficient palladium-catalyzed trifluoromethylthiolation of chelation-assisted C–H bonds has been accomplished by employing a readily accessible trifluoromethylthiolating reagent. The reaction tolerates various directing groups and functional groups and allows the access to diverse trifluoromethylthiolated arenes in good yield. A plausible mechanism was proposed based on preliminary mechanistic investigations.
General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides
Wang, Xin,Zhu, Ming-Hui,Schuman, David P.,Zhong, Dayou,Wang, Wen-Yan,Wu, Lin-Yang,Liu, Wei,Stoltz, Brian M.,Liu, Wen-Bo
supporting information, p. 10970 - 10974 (2018/09/06)
Herein we describe a general, mild and scalable method for deuterium incorporation by potassium methoxide/hexamethyldisilane-mediated dehalogenation of arylhalides. With CD3CN as a deuterium source, a wide array of heteroarenes prevalent in pharmaceuticals and bearing diverse functional groups are labeled with excellent deuterium incorporation (>60 examples). The ipso-selectivity of this method provides precise access to libraries of deuterated indoles and quinolines. The synthetic utility of our method has been demonstrated by the incorporation of deuterium into complex natural and drug-like compounds.
Rhodium-Catalyzed Direct C-H Bond Cyanation in Ionic Liquids
Lv, Songyang,Li, Yaling,Yao, Tian,Yu, Xinling,Zhang, Chen,Hai, Li,Wu, Yong
supporting information, p. 4994 - 4997 (2018/08/24)
A Cp?Rh(III)/IL-based direct C-H bond cyanation system was developed for the first time. The system is a mild, efficient, and recyclable method for the synthesis of aryl nitriles. Many different directing groups can be used in this cyanation, and the reaction tolerates a variety of functional groups.
Method for preparing deuterated aromatic organic compound
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Paragraph 0104-0106, (2017/08/29)
The invention provides a method for preparing a deuterated aromatic organic compound. The method comprises the following steps: firstly, dissolving a halogenated aromatic compound and an alkali metal salt MA into a deuterated solvent or a mixed solvent of the deuterated solvent and a common solvent, dropping an organic silicon reagent, performing stirring reaction at minus 40 DEG C to 150 DEG C, and performing separation purification after reaction, thereby obtaining the deuterated aromatic organic compound. By adopting the method, the deuterated aromatic organic compound can be efficiently, economically and environment-friendly prepared without participation of a transition metal or a metallic tin reagent, and the deuteration rate of the prepared deuterated product is greater than 95%. The method is gentle in condition, good in substrate universality and high in yield, and the prepared deuterated compound can be widely applied to fields of medicine chemistry and organic chemistry.
Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C?H Bonds
Barday, Manuel,Janot, Christopher,Halcovitch, Nathan R.,Muir, James,A?ssa, Christophe
supporting information, p. 13117 - 13121 (2017/10/11)
The functionalization of carbon–hydrogen bonds in non-nucleophilic substrates using α-carbonyl sulfoxonium ylides has not been so far investigated, despite the potential safety advantages that such reagents would provide over either diazo compounds or their in situ precursors. Described herein are the cross-coupling reactions of sulfoxonium ylides with C(sp2)?H bonds of arenes and heteroarenes in the presence of a rhodium catalyst. The reaction proceeds by a succession of C?H activation, migratory insertion of the ylide into the carbon–metal bond, and protodemetalation, the last step being turnover-limiting. The method is applied to the synthesis of benz[c]acridines when allied to an iridium-catalyzed dehydrative cyclization.
Directed C?H Activation and Tandem Cross-Coupling Reactions Using Palladium Nanocatalysts with Controlled Oxidation
Kim, Kiseong,Jung, Younjae,Lee, Suyeon,Kim, Mijong,Shin, Dongwoo,Byun, Hyeeun,Cho, Sung June,Song, Hyunjoon,Kim, Hyunwoo
supporting information, p. 6952 - 6956 (2017/06/06)
Controlled oxidation of palladium nanoparticles provided high-valent PdIV oxo-clusters which efficiently promote directed C?H halogenation reactions. In addition, palladium nanoparticles can undergo changes in oxidation states to provide both high-valent PdIV and low-valent Pd0 species within one system, and thus a tandem reaction of C?H halogenation and cross-coupling (C?N, C?C, and C?S bond formation) was successfully established.
