13677-46-8Relevant academic research and scientific papers
Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
Zhuang, Hongfeng,Lu, Nan,Ji, Na,Han, Feng,Miao, Chengxia
, p. 5461 - 5472 (2021/09/29)
Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).
Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant
Sai, Masahiro
, p. 3482 - 3487 (2018/09/14)
The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 3368 - 3376 (2017/05/22)
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
Li, Xue-Dong,Xie, Li-Jun,Kong, De-Long,Liu, Li,Cheng, Liang
, p. 1873 - 1880 (2017/03/10)
A convenient and regioselective cross-coupling of heteroaryl boronic acids with allylic alcohols under catalyst-free reaction conditions is described. The developed procedure is simple, works under external oxidant- and metal-free conditions, and proves to be very general with an unprecedented ortho-selectivity. This approach represents one of the very few examples of ortho-functionalization of boronic acids.
