3555-84-8Relevant academic research and scientific papers
A new efficient method for the preparation of intermediate aromatic ketones by Friedel–Crafts acylation
Jin, Xiaojun,Wang, Ailing,Cao, Hongyu,Zhang, Shujia,Wang, Lihao,Zheng, Xueliang,Zheng, Xuefang
, p. 5521 - 5530 (2018/04/30)
Abstract: As the most important method to prepare pharmaceutical and chemical intermediate aromatic ketones, Friedel–Crafts (F–C) acylation is used to seek a novel catalytic system which is imminently consistent with the concept of green chemistry. In this study, six deep eutectic solvents (DES) were synthesized for the Friedel–Crafts acylation reaction as a catalytic solvent. Among the six DES, choline chloride-zinc chloride ([ChCl][ZnCl2]2) proved to be the most competent candidate of electron-rich arenes with acylation reagent. It got the highest yield when 1.0 equivalent of [ChCl][ZnCl2]2 used with acyl halides at 70?°C. Recycled DES was reused directly without any extra process. After five cycles, the catalytic activity did not decrease significantly (80–85%). Finally, according to experimental validation, the possible mechanism of this reaction was considered. Graphical Abstract: [Figure not available: see fulltext.].
Synthesis of diaryl ketones through oxidative cleavage of the C-C double bonds in N -Sulfonyl enamides
Kim, Hyunseok,Park, Sangjune,Baek, Yonghyeon,Um, Kyusik,Han, Gi Uk,Jeon, Da-Hye,Han, Sang Hoon,Lee, Phil Ho
, p. 3486 - 3496 (2018/04/14)
An oxidative cleavage of a C-C double bond is developed from the photochemical [2+2]-cycloaddition of diaryl N-tosyl enamides, aryl heteroaryl N-tosyl enamides, and N-tosyl cyclic enamides with singlet molecular oxygen, followed by a ring-opening reaction mediated by Cs2CO3 under air and sunlight without the use of photosesitizer, producing symmetrical and unsymmetrical diaryl, heterodiaryl, and cyclic ketones in good to excellent yields. Moreover, the oxidative cleavage of C-C triple bonds from 1-alkynes is demonstrated for the synthesis of symmetrical and unsymmetrical ketones from the Cu-catalyzed [3+2]-cycloaddition, Rh-catalyzed alkoxyarylation, photooxygenation, and ring-opening reaction in one-pot. Because the synthesis of the symmetrical and unsymmetrical diaryl and/or heterodiaryl ketones bearing an electron-donating group is not easy, the present method is notable.
COMPOUND AND COMPOSITION CONTAINING THE SAME, AND METHOD FOR MANUFACTURING DEVICE USING THE COMPOSITION
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Paragraph 0152-0154, (2017/09/14)
PROBLEM TO BE SOLVED: To provide a compound which efficiently absorbs extreme ultraviolet radiation (EUV) such as KrF excimer laser and ArF excimer laser or an electron beam, has low sensitivity to OoB, and has high contrast. SOLUTION: A compound is represented by formula (1) and formula (2). In formulae (1) and (2), R1a and R1a are each independently a first monovalent organic group containing a divalent hydrocarbon group selected from an alkylene group; a group bonded directly to sulfur atom (S+) is the divalent hydrocarbon group; R2 is a hydrogen atom, an alkyl group and the like; R3 to R6 are a hydrogen atom, a hydroxy group or a second monovalent organic group; X- is a monovalent anion; and R1a and R1b in Formula (1) or R1a and R1b in Formula (2) may be bonded to each other to form a ring. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
supporting information, p. 12337 - 12340 (2017/11/20)
p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis
McManus, Joshua B.,Nicewicz, David A.
, p. 2880 - 2883 (2017/03/11)
Methods for the direct C-H functionalization of aromatic compounds are in demand for a variety of applications, including the synthesis of agrochemicals, pharmaceuticals, and materials. Herein, we disclose the construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere. The reaction proceeds at room temperature under mild conditions and has proven to be compatible with a variety of electron-donating and -withdrawing groups, halogens, and nitrogen- and oxygen-containing heterocycles, as well as aromatic-containing pharmaceutical agents.
An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation
Doan, Tan L. H.,Dao, Thong Q.,Tran, Hai N.,Tran, Phuong H.,Le, Thach N.
supporting information, p. 7875 - 7880 (2016/05/24)
A zirconium-based metal-organic framework, an effective heterogeneous catalyst, has been developed for the Friedel-Crafts benzoylation of aromatic compounds under microwave irradiation. Constructed by a Zr(iv) cluster and a linker 1,4-bis(2-[4-carboxyphenyl]ethynyl)benzene (H2CPEB), the MOF, possessing large pores and high chemical stability, was appropriate for the enhancement of Lewis acid activity under microwave irradiation. The reaction studies demonstrated that the material could give high yields for a few minutes and maintain its reactivity and structure over several cycles.
Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction
Vekariya, Rakesh H.,Aubé, Jeffrey
supporting information, p. 3534 - 3537 (2016/08/16)
The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.
Nickel-catalyzed diaryl ketone synthesis by N-C cleavage: Direct negishi cross-coupling of primary amides by site-selective N,N-Di-boc activation
Shi, Shicheng,Szostak, Michal
, p. 5872 - 5875 (2016/11/29)
A general Negishi acylation of primary amides enabled by a combination of site-selective N,N-di-Boc activation and nickel catalysis is reported for the first time. The reaction is promoted by a bench-stable, inexpensive Ni catalyst. The reaction shows excellent functional group compatibility, affording functionalized diaryl ketones by selective N-C cleavage. Most notably, this protocol represents the first amide cross-coupling by direct metal insertion of simple and readily available primary amides. The overall strategy by N,N-di-Boc activation/metal insertion is suitable for a broad range of coupling protocols via acylmetals. Mechanistic experiments suggest high reactivity of N,N-di-Boc activated 1° amides in direct amide C-N cross-couplings.
Carbonylative coupling of aryl tosylates/triflates with arylboronic acids under CO atmosphere
Hao, Cheng Yi,Wang, Dan,Li, Ya Wei,Dong, Lin Lin,Jin, Ying,Zhang, Xiu Rong,Zhu, He Yun,Chang, Sheng
, p. 86502 - 86509 (2016/09/23)
The carbonylative Suzuki-Miyaura reaction between aryl tosylates/triflates with arylboronic acid is herein reported, using base-free conditions and a balloon pressure of carbon monoxide. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of oxybenzone and ketoprofen in good yields under mild conditions.
Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon–Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect
Shi, Shicheng,Szostak, Michal
, p. 10420 - 10424 (2016/07/21)
The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C?N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)2Cl2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N?C bond activation accomplished to date (room temperature, 10 min). Considering the versatile role of polyfunctional biaryl ketone linchpins in modern organic synthesis, availability, and excellent functional-group tolerance of organozinc reagents, this strategy provides a new platform for amide N?C bond/organozinc cross-coupling under mild conditions.
