6609-59-2Relevant academic research and scientific papers
Metal-Free Etherification of Aryl Methyl Ether Derivatives by C-OMe Bond Cleavage
Wang, Xueqiang,Li, Chenchen,Wang, Xia,Wang, Qingli,Dong, Xiu-Qin,Duan, Abing,Zhao, Wanxiang
, p. 4267 - 4272 (2018/07/29)
A general and efficient protocol was developed for the synthesis of aryl alkyl ethers through metal-free C-OMe bond cleavage under mild reaction conditions. This process displays a wide scope of methoxyarenes and alcohols, including primary, secondary, and tertiary alcohols, as well as natural products, pharmaceuticals, and biologically active alcohols. DFT calculations and experimental results simultaneously confirm that a potassium ion plays a critical role in the activation of methoxy group via binding with the nitrile and provide support for an SNAr mechanism.
N-Heterocyclic carbene-mediated redox condensation of alcohols
Kato, Terumasa,Matsuoka, Shin-Ichi,Suzuki, Masato
supporting information, p. 8569 - 8572 (2016/07/13)
N-Heterocyclic carbenes (NHCs) with a variety of oxidants promote the Mitsunobu-type coupling reactions of alcohols with phenols, carboxylic acids, and phthalimide. Experiments using a chiral alcohol indicate that these reactions proceed via SN1 or SN2 pathways depending on the polarity of the used solvents. The NHCs are consumed as reducing reagents to form their oxides as readily separable byproducts.
Two ways of preparing benzonitriles using BrCCl3-PPh3 as the reagent
Jasem, Yosef Al,Barkhad, Mohamed,Khazali, Mona Al,Butt, Hifsa Pervez,El-Khwass, Noha Ashraf,Azani, Mariam Al,Hindawi, Bassam Al,Thiemann, Thies
, p. 80 - 84 (2014/03/21)
Benzamides were converted into benzonitriles with BrCCl3- PPh3-Et3N in CH2Cl2 in an Appel-type reaction. Benzaldoximes could be transformed to benzonitriles under identical conditions. It was found that the reaction system BrCCl3-(2 equiv.)PPh3 was also suitable for these transformations with PPh 3 replacing Et3N.
Copper-mediated cyanation of aryl halides by activation of benzyl cyanide as the cyanide source
Wen, Qiaodong,Jin, Jisong,Mei, Yuncai,Lu, Ping,Wang, Yanguang
, p. 4032 - 4036 (2013/07/11)
Aryl nitriles were efficiently synthesized through copper-mediated cyanation of aryl halides using benzyl cyanide as the cyanide source. Aryl halides with various substituents on the aromatic ring afforded the corresponding aryl nitriles in 32-97 % yields (25 examples). This reaction could also be carried on a gram scale by using commercially available reagents. Additionally, a C-H bond oxidation and a C-CN cleavage are proposed to be involved in this cascade process. An efficient, copper-mediated cascade synthesis of aryl nitriles from aryl halides using benzyl cyanide as the cyanide source is described. Compared with traditional copper-mediated cyanation reactions, this approach effectively avoided the use of toxic MCN and low soluble reagents. Furthermore, C-H oxidation and C-CN cleavage are proposed to be involved in this cascade process. Copyright
