4023-77-2Relevant academic research and scientific papers
Flexible Construction of Functionalized-Pyrroles under Palladium or Copper Catalysis in the Presence of BF3 ? Et2O
Liu, Yin,Liu, Teng,Yan, Biwei,Wei, Kun,Guo, Wusheng
, p. 916 - 921 (2022/01/26)
We have developed a flexible approach enabling the access to highly functionalized pyrroles under palladium or copper catalysis in the presence of BF3 ? Et2O. This catalytic methodology utilizes commercially available amines as react
Rhodium(I)-Catalyzed CO-Gas-Free Arylative Dual-Carbonylation of Alkynes with Arylboronic Acids via the Formyl C-H Activation of Formaldehyde
Morimoto, Tsumoru,Wang, Chuang,Tanimoto, Hiroki,Artok, Levent,Kakiuchi, Kiyomi
, p. 3372 - 3382 (2021/05/04)
The rhodium(I)-catalyzed reaction of alkynes with aryl boronic acids in the presence of formaldehyde results in a CO-gas-free arylative dual-carbonylation to produce γ-butenolide derivatives. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis. The former complex catalyzes the abstraction of a carbonyl moiety from formaldehyde through the activation of its formyl C-H bond (decarbonylation) and the latter catalyzes the subsequent dual-incorporation of the resulting carbonyl unit (carbonylation). The use of larger amounts of the phosphine-ligated rhodium(I) complex generates more carbonyl units, leading to the formation γ-butenolides via the dual-incorporation of the carbonyl unit.
Transition-metal-free and base promoted C-C bond formationviaC-N bond cleavage of organoammonium salts
Chen, Tieqiao,Huang, Tianzeng,Ke, Yuting,Li, Chunya,Liu, Long,Tang, Yuanyuan,Tang, Zhi,Wang, Kunyu,Zhang, Tao
supporting information, p. 8237 - 8240 (2021/10/12)
A transition-metal-free and base promoted C-C bond forming reaction of benzyl C(sp3)-H bond with organoammonium saltsviaC-N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl ammonium salt could couple readily with various benzyl C(sp3)-H species, producing the corresponding products in moderate to excellent yields with good functional group tolerance. Late stage chemical manipulation enabled the specific 1,2-diarylethane structure of products transformed into useful olefin compoundsviadehydrogenation, which further demonstrated the utility of this reaction.
Method for synthesizing alpha, beta unsaturated ketone
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Paragraph 0016-0022, (2021/10/11)
The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for synthesizing alpha, beta unsaturated ketone. The reaction adopts a synergetic catalysis system of Co(acac)2 or Co(acac)3, a ligand and AlMe3, provides a way for economically and selectively synthesizing alpha, beta unsaturated ketones by atoms, and has the advantages of high yield and wide substrate range.
Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis
Baik, Mu-Hyun,Choi, Seulhui,Hong, Soon Hyeok,Lee, Geun Seok,Won, Joonghee
, p. 16933 - 16942 (2020/08/03)
The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.
Heterogeneous gold-catalyzed oxidative cross-coupling of propargylic acetates with arylboronic acids leading to (E)-α-arylenones
Liu, Dayi,Nie, Quan,Zhang, Rongli,Cai, Mingzhong
supporting information, p. 29 - 34 (2018/11/30)
An efficient heterogeneous gold-catalyzed oxidative cross-coupling of propargylic acetates with arylboronic acids has been developed that proceeds smoothly in the presence of Selectfluor and provides a general and powerful tool for the preparation of various valuable α-arylenones with moderate to good yields, excellent E-selectivity, and recyclability of the gold catalyst. The reaction is the first example of heterogeneous gold-catalyzed arylative rearrangement of propargylic acetates for construction of complex enones.
Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts
Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Lázaro-Milla, Carlos
, p. 2177 - 2186 (2017/02/26)
A selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.
Preparation method of alpha, beta-diphenyl-1-aryl-acrylketone compound
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Paragraph 0056-0059, (2018/02/27)
The invention belongs to the technical field of organic compound synthesis and particularly relates to a preparation method of an alpha, beta-diphenyl-1-aryl-acrylketone compound. According to the preparation method, in an organic solvent, diphenylcyclopropenone with structure as shown in a formula (I) and arylboronic acid with structure as shown in a formula (II) are taken as reaction materials, and the alpha, beta-diphenyl-1-aryl-acrylketone compound with structure as shown in a formula (III) is obtained through ring-opening reaction of cycolpropenone in the presence of a palladium catalyst; and in the formula (II) and the formula (III), R is independently selected from one of H, methyl, chlorine, trifluoromethyl, phenoxy, vinyl, fluorine, a formyl group, isopropyl, n-propyl, cyan, tertiary butyl, nitro or phenyl.
Palladium-catalyzed dehydrogenative β-arylation of simple saturated carbonyls by aryl halides
Gandeepan, Parthasarathy,Rajamalli,Cheng, Chien-Hong
, p. 4485 - 4489 (2015/01/09)
(Chemical Equation Presented) A versatile palladium-catalyzed synthesis of highly substituted α,β-unsaturated carbonyl compounds has been developed. In contrast to the known Heck-type coupling reaction of unsaturated carbonyl compounds with aryl halides, the present methodology allows the use of stable and readily available saturated carbonyl compounds as the alkene source. In addition, the reaction proceeds well with low catalyst loadings and does not require any expensive metal oxidants or ligands. A variety of saturated aldehydes, ketones, and esters are compatible for the reaction with aryl halides under the developed reaction conditions to afford α,β-unsaturated carbonyl compounds in good to excellent yields. A possible reaction mechanism involves a palladium-catalyzed dehydrogenation followed by Heck-type cross couplings.
Rhodium(I)-catalyzed carbonylative arylation of alkynes with arylboronic acids using formaldehyde as a carbonyl source
Wang, Chuang,Morimoto, Tsumoru,Kanashiro, Hiroyuki,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi,Artok, Levent
supporting information, p. 1155 - 1159 (2014/05/20)
The rhodium(I)-catalyzed reaction of alkynes with arylboronic acids in the presence of formaldehyde resulted in a carbon monoxide gas-free carbonylative arylation to yield α,β-enones. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis, which catalyze the abstraction of a carbonyl moiety from formaldehyde (decarbonylation) and its subsequent introduction into the substrate (carbonylation), respectively. Georg Thieme Verlag Stuttgart New York.
