6933-25-1Relevant academic research and scientific papers
Selective oxidation of alkenes to carbonyls under mild conditions
Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan
supporting information, p. 5549 - 5555 (2021/08/16)
Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.
Photo-induced oxidative cleavage of C-C double bonds of olefins in water
Zhang, Yilan,Yue, Xiaoguang,Liang, Chenfeng,Zhao, Jianming,Yu, Wenbo,Zhang, Pengfei
supporting information, (2021/08/27)
The carbonyl compounds, synthesized by the oxidative cleavage of their corresponding olefins, are of great significance in organic synthesis, especially aryl ketones. We have developed a gentle and effective protocol, using acid red 94 as the organic metal-free photocatalyst, O2 as the oxidant, and water as the solvent. Under visible light irradiation, aryl ketone derivatives were obtained in moderate to excellent yields, showing good economic and environmental advantages.
Aryl aldiketone and synthesis method thereof
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Paragraph 0033, (2021/09/26)
The invention discloses an aryl aldehyde ketone and a synthesis method thereof, wherein an aryl aldehyde is synthesized from cheap olefin as a raw material. A commercially available inexpensive olefin is used as a raw material, ether is used as an additive, molecular oxygen serves as a sole oxidizing agent, water is used as a solvent, and the aldehyde and ketone are synthesized by column chromatography under a photocatalytic condition. The invention has the advantages of mild reaction conditions, green and environmental protection, simple experimental operation, good reaction selectivity, high product yield and the like.
Palladium-Catalyzed Amide N-C Hiyama Cross-Coupling: Synthesis of Ketones
Idris, Muhammad Aliyu,Lee, Sunwoo
supporting information, p. 9190 - 9195 (2020/11/18)
N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a broad substrate scope and showed good functional group tolerance. N-Benzoylsuccinimide and N-protected N-phenylbenzamides showed good activities in coupling reactions with phenylsiloxane. The employment of CuF2 as an activor afforded the decarbonylative products at 160 °C.
Highly efficient synthesis of aryl ketones by PEPPSI-palladium catalyzed acylative Suzuki coupling of amides with diarylborinic acids
Wang, Chen,Huang, Lingyun,Wang, Fengze,Zou, Gang
supporting information, p. 2299 - 2301 (2018/05/16)
An improved acylative cross-coupling of various N-methyl-N-tosyl amides with diarylborinic acids for synthesis of aryl ketones is developed. In most cases, aryl ketones could be obtained in excellent yields by using 1 mol% 2,6-diisopropylphenylimidazolylidene and 3-chloropyridine co-supported palladium chloride as catalyst in the presence of 3 equiv. K2CO3 as base in refluxing THF. The readily prepared and cost-effective substrates, N-methyl-N-tosylamides and diarylborinic acids, and the commercially available catalyst system promise a practical and efficient access to aryl ketones.
A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation
Kinney, R. Garrison,Tjutrins, Jevgenijs,Torres, Gerardo M.,Liu, Nina Jiabao,Kulkarni, Omkar,Arndtsen, Bruce A.
, p. 193 - 199 (2018/02/06)
The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.
Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones
Hao, Wenyan,Liu, Haiyi,Yin, Lin,Cai, Mingzhong
, p. 4244 - 4251 (2016/06/09)
A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.
One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling
Wu, Hongxiang,Xu, Baiping,Li, Yue,Hong, Fengying,Zhu, Dezhao,Jian, Junsheng,Pu, Xiaoer,Zeng, Zhuo
, p. 2987 - 2992 (2016/04/26)
A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min. (Chemical Equation Presented).
A versatile method for the synthesis of diaryl and alkyl aryl ketones via palladium-catalysed cross-coupling reaction of arylboronic acids with acyl chlorides
Rafiee, Fatemeh,Hajipour, Abdol R.
, p. 181 - 184 (2015/03/30)
An efficient catalytic system using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride and PdCl2 was developed for the cross-coupling reaction of arylboronic acids with acyl chlorides. The catalytic amount of this homogeneous catalytic system affords the corresponding diaryl and alkyl aryl ketones in good to excellent yields under mild reaction conditions.
An efficient and recyclable thermoregulated phosphine-palladium catalyst for the carbonylative Suzuki coupling of aryl halides with arylboronic acids in water
Hao, Yuanping,Jiang, Jingyang,Wang, Yanhua,Jin, Zilin
, p. 106 - 110 (2015/09/28)
An efficient protocol has been developed for the carbonylative Suzuki coupling of aryl halides using the thermoregulated phosphine-palladium as a reusable catalyst in pure water. This protocol was applied to a wide variety of hindered and functionalized aryl iodides and bromides with arylboronic acids, to afford the desired biaryl ketones in good to high yields. The palladium catalyst was easily recovered in the aqueous phase and reused up to eight cycles without a significant decrease in its activity.
