26954-31-4Relevant academic research and scientific papers
Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane
Chen, Xue,Jin, Hongwei,Liu, Yunkui,Wang, Zhen,Zhou, Bingwei,Zhou, Jinyong
supporting information, p. 8021 - 8024 (2021/10/04)
Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific
Visible-Light Photoredox-Catalyzed α-Allylation of α-Bromocarbonyl Compounds Using Allyltrimethylsilane
Gontala, Arjun,Jang, Gwang Seok,Woo, Sang Kook
supporting information, p. 506 - 509 (2021/01/20)
The development of a greener allylation reagent for α-allylation of carbonyl compounds is of great necessity. Here we present allyltrimethylsilane as a novel allylation reagent in the photoredox-catalyzed α-allylation of carbonyl compounds such as ketones, esters, and amides. The reaction process shows good functional group tolerance and generates a good yield of the product. The reaction mechanism is a radical-mediated reaction by photo-induced single electron transfer.
Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification
Li, Na,Sun, Baozhen,Liu, Shuang,Zhao, Jinbo,Zhang, Qian
supporting information, p. 190 - 193 (2020/01/02)
A straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines is realized by Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of a commercially available bisphosphine ligand. The enantioenriched products can be facilely converted to functionalized alcohols with high fidelity of chiral transfer.
Iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines
Wang, Hai,Wu, Xiao-Feng,Yin, Zhiping,Zhang, Youcan
supporting information, p. 7045 - 7048 (2020/07/14)
Herein, a new method of iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines has been developed. By using readily available substrates, 32 examples of functionalized pyrrolines were prepared in moderate to good yields. Notably, examples of reduction and cycloaddition reactions of the obtained product were given as well. This journal is
Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Zhang, Mengru,Liu, Shuang,Li, Hexin,Guo, Yajing,Li, Na,Guan, Meihui,Mehfooz, Haroon,Zhao, Jinbo,Zhang, Qian
supporting information, p. 12620 - 12627 (2019/09/16)
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.
Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization
Usami, Kaoru,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 5714 - 5717 (2018/09/21)
The treatment of an O-(4-methoxybenzyl) oxime ether bearing an olefin substituent and 1-chloroanthraquinone (1-Cl-AQN) catalyst in 2-butanone under visible-light irradiation affords pyrroline via an iminyl radical intramolecular hydroimination. Mechanistic studies indicate that iminyl radical generation mainly proceeds by hydrogen abstraction of the photocatalyst from the benzyl position of the oxime. Moreover, the hydrogen atom was identified in circulation from the benzylic position of the substrates between AQN and 2-butanone to quench the carbon radical without requiring any additional reagents.
Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4
MacNair, Alistair J.,Tran, Ming-Ming,Nelson, Jennifer E.,Sloan, G. Usherwood,Ironmonger, Alan,Thomas, Stephen P.
supporting information, p. 5082 - 5088 (2014/07/08)
An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.
Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
Gómez-Suárez, Adrián,Gasperini, Danila,Vummaleti, Sai V.C.,Poater, Albert,Cavallo, Luigi,Nolan, Steven P.
, p. 2701 - 2705 (2014/08/18)
We report a new catalytic protocol for the synthesis of γ,δ-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON an
Pd-catalyzed domino carbonylative-decarboxylative allylation: An easy and selective monoallylation of ketones
Giboulot, Steven,Liron, Frederic,Prestat, Guillaume,Wahl, Benoit,Sauthier, Mathieu,Castanet, Yves,Mortreux, Andre,Poli, Giovanni
, p. 5889 - 5891 (2012/07/28)
In the presence of an allyl alcohol, α-chloroacetophenones undergo an allyloxycarbonylation reaction followed by in situ decarboxylative allylation to selectively afford the corresponding monoallylated ketones via a Pd-catalyzed domino sequence. The scope of the reaction was extended to substituted α-chloroacetophenones as well as various allyl alcohols.
Synthesis of 2-arylcycloalka-2,4-dienones using sulfone-based methodology
Hok, Saphon,Schore, Neil E.
, p. 1736 - 1738 (2007/10/03)
Addition of the anion derived from (phenylthiomethyl)phenyl sulfone to a selection of aryl ω-alkenyl ketones gives adducts that via a sequence of Lewis acid catalyzed rearrangement, α-allylation, and metathesis give rise to 2-thio-4-cycloalkenones. These in turn give cycloalkadienones upon oxidation and elimination. An attempt to develop a polymer-supported variant fails because of the reversibility of sulfone anion addition.
