27383-92-2Relevant academic research and scientific papers
Studies on Copper(II) Complexes of ortho-Quinone Mono-oximes: Reaction of Bis(4-chloro-1,2-benzoquinone 2-oximato)copper(II) with Dimethyl Acetylenedicarboxylate under Various Experimental Conditions
Castellani, Carla Bisi,Millini, Roberto
, p. 1461 - 1462 (1984)
In anhydrous methanol the title complex reacts with dimethyl acetylenedicarboxylate to give methyl 5-chloro-1,3-benzoxazole-2-carboxylate instead of 6-chloro-4-hydroxy-2,3-dimethoxycarbonyl-1,4-benzoxazine as in aqueous solution.The role of water in such
Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives
Lee, Mijung,Hwang, Young Kyu,Kwak, Jaesung
, p. 3136 - 3144 (2021/09/30)
CO2utilization is an attractive aspect as it allows the direct conversion of CO2into valuable chemicals. In this regard, direct incorporation of CO2into the C-H bond of heteroaromatic compounds is important due to the ubiquitous structural motifs of the heteroaromatic carboxylic acids. Herein, we report the Ag-catalyzed C-H carboxylation of thiophene derivatives. This new catalytic system involving a phosphine ligand and lithiumtert-butoxide enables the direct carboxylation of thiophenes under mild reaction conditions. Experimental studies revealed that the use oftert-butyl alkoxide is critical for the exergonic formation of an arylsilver intermediate, and the results were further supported by density functional theory calculations.
Binuclear molybdenum alkoxide as the versatile catalyst for the conversion of carbon dioxide
Chen, Jing-Huo,Deng, Cheng-Hua,Fang, Sheng,Ma, Jian-Gong,Cheng, Peng
, p. 989 - 996 (2018/03/13)
The triply bonded dimolybdenum compound, Mo2(OtBu)6 (1), was investigated as a homogeneous catalyst for the conversion of CO2. The compound 1 acted as a rare example of a versatile catalyst with an impressive ability to transform CO2 into various valuable products, including propiolic acids, cyclic carbonates, and benzo[d]thiazole- and benzo[d]oxazolecarboxylic acids, in high yields with short reaction times and excellent selectivity at ambient pressure and low temperatures (25-75 °C). This is the first report of the application of a metal-metal bond-containing species in the catalytic conversion of CO2.
Method of synthesizing heteroaromatic formic ether compound
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Paragraph 0038, (2017/08/19)
The invention discloses a method of synthesizing a heteroaromatic formic ether compound. By taking midazolium chloride salt of which the molecular formula is [(ArN=C(CH3)NCH2CH2NCH2C6H5)CH]Cl (wherein Ar is equal to 2,6-bi-CH(CH3)2-C6H3) as a catalyst, the heteroaromatic formic ether compound is synthesized through carboxylation reaction of a heteroaromatic compound and carbon dioxide at atmospheric pressure. The heteroaromatic formic ether compound is a first example that is catalyzed by imidazolium salt and prepared through the carboxylation reaction of the heteroaromatic compound and carbon dioxide. Compared with the prior art, the catalyst is green, the synthesis is easier, reaction conditions are mild, and the heteroaromatic formic ether compound has equivalent or better catalytic activity and functional group tolerance.
C-H carboxylation of heteroarenes with ambient CO2
Fenner, Sabine,Ackermann, Lutz
supporting information, p. 3804 - 3807 (2016/07/07)
The C-H carboxylation of heteroarenes was achieved under transition metal-free reaction conditions with naturally abundant CO2 as the C1 source at relatively low temperature. The C-H carboxylation was mediated by KOt-Bu at atmospheric pressure
PH-Responsive N-heterocyclic carbene copper(i) complexes: Syntheses and recoverable applications in the carboxylation of arylboronic esters and benzoxazole with carbon dioxide
Wang, Wenlong,Zhang, Guodong,Lang, Rui,Xia, Chungu,Li, Fuwei
supporting information, p. 635 - 640 (2013/03/29)
A pH-controlled monophasic/biphasic switchable system has been developed as a green and novel strategy for homogeneous catalyst recycling, which has been successfully applied to the Cu-NHC-catalyzed carboxylation of organoboronic esters and benzoxazole with carbon dioxide. Additionally, the present strategy could also be extended to the Ag-NHC-catalyzed carboxylation of terminal alkyne. The tertiary amine-functionalized catalysts could be used for at least four times with a slight loss of activity.
Direct C-H carboxylation with carbon dioxide using 1,2,3-triazol-5-ylidene copper(I) complexes
Inomata, Hiroshi,Ogata, Kenichi,Fukuzawa, Shin-Ichi,Hou, Zhaomin
, p. 3986 - 3989 (2012/09/10)
1,2,3-Triazol-5-ylidene copper(I) complexes (tzNHC-Cu) efficiently catalyzed the direct C-H carboxylation of benzoxazole and benzothiazole derivatives with CO2 to give the corresponding esters in excellent yields after treatment with alkyl iodi
Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles
Vechorkin, Oleg,Hirt, Nathalie,Hu, Xile
supporting information; experimental part, p. 3567 - 3569 (2010/10/02)
(Equation Presented). A simple and straightforward method has been developed for the direct carboxylation of aromatic heterocylces such as oxazoles, thiazoles, and oxadiazoles using CO2 as the C1 source. The reactions require no metal catalyst and only Cs2CO3 as the base. A good functional group tolerance is achieved.
Reaction of 1,2-Quinone Monooximes and their Metal Complexes with Dimethyl Acetylenedicarboxylate
Barjesteh, H.,Brain, E. G.,Charalambous, J.,Gaganatsou, P.,Thomas, T. A.
, p. 2701 - 2720 (2007/10/03)
1,2-Quinone monooximes (1) and their metal complexes (2) react with dimethyl acetylenedicarboxylate (DMAD) under relatively mild conditions to give 1,4-oxazines (3) or 1,4-oxazin-2-ones (4) or the nucleophilic 1,2-addition products (Z)- and (E)-1,2-benzoquinone 1-oxime> (5 and 6).The complexes (2) also catalyse the aerobic oxidation of the 1,4-oxazines to the corresponding 1,3-oxazoles (7).Relationships between the nature of the products isolated, the metal ion present, the ring substituent and the reaction conditions employed have been observed.Thus the reactions involving the transition metal complexes give rise to cycloadducts while the main group metal complexes afford open-chain 1,2-addition products.Of the 1,2-quinone monooximes studied only the 4-bromo, 4-chloro and 4-methyl substituted compounds give 1,4-oxazin-2-ones.
A SIMPLE ONE-STEP SYNTHESIS OF ALKYL BENZAZOL-2-CARBOXYLATES
Musser, J. H.,Hudec, T. T.,Bailey, K.
, p. 947 - 954 (2007/10/02)
A simple one-step synthesis of alkyl benzazol-2-carboxylates employing alkyl trialkoxyacetate is described.
