42160-93-0Relevant academic research and scientific papers
Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones
Samser, Shaikh,Biswal, Priyabrata,Meher, Sushanta Kumar,Venkatasubbaiah, Krishnan
, p. 1386 - 1394 (2021/02/27)
One-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol result in the formation of 1,5-diketone products. This simple one-pot method avoids the use of highly electrophilic vinyl ketones.
Synthesis of chiral seven-membered β-substituted lactams: Via Rh-catalyzed asymmetric hydrogenation
Huang, Yi,Li, Pan,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 8819 - 8823 (2018/11/30)
Rh/bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of seven-membered β-substituted α,β-unsaturated lactams was successfully developed to prepare various chiral seven-membered β-substituted lactams with good to excellent results (up to >99% conversion, 99% yield, and >99% ee).
Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α, β-cyclohexenones
Liu, Cheng-Hang,Zhuang, Zhe,Bose, Sritama,Yu, Zhi-Xiang
supporting information, p. 2752 - 2755 (2016/05/19)
A Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes (VCPs) and CO to α, β-cyclohexenones has been developed. The reaction can tolerate aryl and aliphatic groups at the α-position of VCPs, while VCP substrates with vinyl or alkynyl substitutions are not suitable ones. In addition, this reaction can also be used to synthesize bicyclic rings if an aryl group is attached to the vinyl moiety of the substrate. Compared to the Fe(CO)5-mediated [5+1] reaction, the use of cheap and safe Fe2(CO)9 and abandoning the photo-irradiation conditions are the two major advantages of the present method.
Palladium-catalyzed oxidative heck coupling of cyclic enones with simple arenes by C-H activation
Chung, Leung Gulice Yiu,Juwaini, Nur Asyikin Binte,Seayad, Jayasree
, p. 1270 - 1274 (2015/04/27)
A simple catalyst system consisting of Pd(OAc)2 and 3-nitropyridine for the aerobic oxidative Heck coupling of cyclic enones, in particular challenging unsubstituted cyclic enones, with simple arenes by C-H activation was investigated. This novel method was applied to various functionalized arenes and cyclic enones and allowed the synthesis of β-aryl cyclic enones in modest to high yields.
Isopropylmagnesium chloride-promoted unilateral addition of Grignard reagents to β-diketones: One-pot syntheses of β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones
Yuan, Rui,Zhao, Dan,Zhang, Li-Yuan,Pan, Xiang,Yang, Yan,Wang, Pei,Li, Hong-Feng,Da, Chao-Shan
supporting information, p. 724 - 728 (2016/01/12)
The regioselective unilateral additions of Grignard reagents to acyclic or cyclic β-diketones were effectively promoted by sub-stoichiometric amounts of i-PrMgCl to afford β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones, respectively. Also, the addition of Grignard reagents to acyclic β-diketones followed by a reaction with cyclic β-diketones in a one-pot process was put forward. The reaction mechanism was discussed in detail to explain the high regioselectivity via chemical experiments, hydrogen-deuterium exchange and mass spectrometry.
Copper/Selectfluor-System-Catalyzed Dehydration-Oxidation of Tertiary Cycloalcohols: Access to β-Substituted Cyclohex-2-enones, 4-Arylcoumarins, and Biaryls
Ren, Shaobo,Zhang, Jian,Zhang, Jiahui,Wang, Heng,Zhang, Wei,Liu, Yunkui,Liu, Miaochang
supporting information, p. 5381 - 5388 (2015/08/24)
A route to β-substituted cyclohex-2-enones, 4-arylcoumarins, and biaryls has been developed. This approach involves a one-pot Cu0/Selectfluor-catalyzed dehydration-oxidation of tertiary cycloalcohols. Thus, by using 2 equiv. of Selectfluor at 25 C, the dehydration-oxidation of tertiary cyclohexanols and oxabenzocyclohexanols gave β-substituted cyclohex-2-enones and 4-arylcoumarins, respectively; whereas the dehydration-oxidation of tertiary cyclohexanols gave biaryls as the final products by using 2.5 equiv. of Selectfluor at 80 C. A route to β-substituted cyclohex-2-enones, 4-arylcoumarins, and biaryls has been developed. This approach involves a one-pot Cu0/Selectfluor-catalyzed dehydration-oxidation of tertiary cycloalcohols.
Highly enantioselective synthesis of chiral cyclic allylic amines via RH-catalyzed asymmetric hydrogenation
Zhou, Ming,Liu, Tang-Lin,Cao, Min,Xue, Zejian,Lv, Hui,Zhang, Xumu
supporting information, p. 3484 - 3487 (2014/07/21)
Highly regioselective and enantioselective asymmetric hydrogenation of cyclic dienamides catalyzed by an Rh-DuanPhos complex has been developed, which provides a readily accessible method for the synthesis of chiral cyclic allylic amines in excellent enantioselectivities (up to 99% ee). The products are valuable chiral building blocks and could be easily transformed to multisubstituted cyclohexane derivatives.
Ligand- and base-free Pd(II)-catalyzed controlled switching between oxidative heck and conjugate addition reactions
Walker, Sarah E.,Boehnke, Julian,Glen, Pauline E.,Levey, Steven,Patrick, Lisa,Jordan-Hore, James A.,Lee, Ai-Lan
supporting information, p. 1886 - 1889 (2013/06/04)
A simple change of solvent allows controlled and efficient switching between oxidative Heck and conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. Both reactions are ligand- and base-free and tolerant of air and moisture, and the controlled switching sheds light on some of the factors which favor one reaction over the other.
Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α,β- and β,γ-cyclohexenones
Jiang, Guo-Jie,Fu, Xu-Fei,Li, Qian,Yu, Zhi-Xiang
supporting information; experimental part, p. 692 - 695 (2012/03/26)
A cationic Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropanes and CO has been developed, affording either β,γ-cyclohexenones as major products or α,β-cyclohexenones exclusively, under different reaction conditions.
Palladium-catalyzed Mizoroki-Heck-type reaction of aryl trimethoxysilanes
Ye, Zhishi,Chen, Fan,Luo, Fang,Wang, Wenhui,Lin, Baoda,Jia, Xiaofei,Cheng, Jiang
supporting information; experimental part, p. 2198 - 2200 (2011/03/19)
A palladium-catalyzed Mizoroki-Heck-type reaction of aryl trimethoxysilanes with olefins is described. A series of ArSi(OMe)3 and olefins, including electron-rich and electron-deficient analogues worked well in the procedure, affording the arylation products in moderate to good yields. Georg Thieme Verlag Stuttgart.
