40237-72-7Relevant academic research and scientific papers
External oxidant-free alkylation of quinoline and pyridine derivatives
Gao, Xianying,Li, Jingya,Liu, Zhenwei,Luan, Nannan,Shen, Linhua,Wu, Yangjie,Wu, Yusheng,Zou, Dapeng
, p. 1738 - 1742 (2020)
A novel and efficient method for the generation of alkyl radicals and the alkylation of quinoline and pyridine derivatives under mild conditions has been developed. This strategy allows the direct alkylation of heteroaromatics in the absence of an external oxidant. A preliminary mechanistic study suggests that the present reaction probably proceeds via an intermolecular HAT process.
Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature
Venkatesh, Rapelly,Singh, Adesh Kumar,Lee, Yong Rok,Kandasamy, Jeyakumar
, p. 7832 - 7837 (2021/09/28)
Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.
Preparation of alkylated compounds using the trialkylphosphate
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Paragraph 0168-0169; 0171, (2021/11/02)
[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no
Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds
Zhu, Xiaoyi,Li, Ruibo,Yao, Hequan,Lin, Aijun
supporting information, p. 4630 - 4634 (2021/06/28)
A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.
Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates
Banerjee, Amit,Hattori, Tomohiro,Yamamoto, Hisashi
, (2021/06/16)
Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).
Solid-supported Pt-catalyzed remote C-H etherification of arylamines: A simple and practical approach for the synthesis of aromatic ethers
Han, Junfen,Wang, Guodong,Sun, Jian,Li, Hongshuang,Duan, Guiyun,Li, Furong,Xia, Chengcai
, (2019/06/18)
A simple and practical approach for a direct remote C-H etherification of arylamines with alcohol is developed herein by using a solid-supported Pt catalyst, hence providing a valuable method for the synthesis of aromatic ethers. The catalyst can easily b
Transition-Metal-Free Oxidation of Benzylic C-H Bonds of Six-Membered N-Heteroaromatic Compounds
Gao, Xianying,Han, Shuaijun,Zheng, Maolin,Liang, Apeng,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie,Li, Jingya
, p. 4040 - 4049 (2019/04/30)
A novel oxidation of benzylic C-H bonds for the synthesis of diverse six-membered N-heteroaromatic aldehydes and ketones has been developed. The obvious advantages of this approach are the simple operation, mild reaction conditions, and without use of toxic reagent and transition metal. The present method should provide a useful access for the synthesis and modification of N-heterocycles.
Practical preparation of methyl vinyl ethers through the direct coupling of ketones with CHCl2OMe promoted by Mg/TiCl4/THF
Ananthan, Bakthavachalam,Yan, Tu-Hsin
supporting information, p. 753 - 760 (2018/03/12)
Herein we utilized a new methylene carbenoid as an extremely simple and highly practical reagent for the preparation of vinyl ether with good to excellent yield. This method efficiently effects methoxymethylenation or vinyl ether formation of enolizable, nonenolizable, and sterically hindered ketones. The complexation of Ti–Mg–CHOMe was facilitated, presumably, by THF dramatically increasing the feasibility; and scope of this protocol is to produce vinyl ethers which can be used as convenient building blocks for the preparation of biologically useful molecules.
Photocatalytic Dehydrogenative Cross-Coupling of Alkenes with Alcohols or Azoles without External Oxidant
Yi, Hong,Niu, Linbin,Song, Chunlan,Li, Yiying,Dou, Bowen,Singh, Atul K.,Lei, Aiwen
supporting information, p. 1120 - 1124 (2017/01/18)
Direct cross-coupling between alkenes/R-H or alkenes/RXH is a dream reaction, especially without external oxidants. Inputting energy by photocatalysis and employing a cobalt catalyst as a two-electron acceptor, a direct C?H/X?H cross-coupling with H2evolution has been achieved for C?O and C?N bond formation. A new radical alkenylation using alkene as the redox compound is presented. A wide range of aliphatic alcohols—even long chain alcohols—are tolerated well in this system, providing a new route to multi-substituted enol ether derivatives using simple alkenes. Additionally, this protocol can also be used for N-vinylazole synthesis. Mechanistic insights reveal that the cobalt catalyst oxidizes the photocatalyst to revive the photocatalytic cycle.
Pd-Catalyzed Regioselective Decarboxylative/C-H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers
Rouchet, Jean-Baptiste E. Y.,Hachem, Mahmoud,Schneider, Cédric,Hoarau, Christophe
, p. 5363 - 5369 (2017/08/17)
A direct introduction of vinyl ethers into C-H bond of heterocycles is reported. For this purpose, decarboxylative direct C-H cross-coupling of 1,3-diazoles with α-carboxyvinyl ethers as coupling partners was achieved under Pd(0)/Cu(I) cooperative catalysis to produce various α-heteroarylated vinylethers. This methodology was applied to the innovative production of heteroarylated enolizable ketones and naturally occurring bis-oxa(thia)zoles.
