50599-02-5Relevant academic research and scientific papers
Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes
Chen, Mingjie,Li, Wenbo,Wang, Lei,Wang, Yuzhuo,Zhang, Junliang,Zhang, Kenan
supporting information, p. 4421 - 4427 (2020/02/11)
Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u
Green organocatalytic synthesis of isoxazolines via a one-pot oxidation of allyloximes
Triandafillidi, Ierasia,Kokotos, Christoforos G.
supporting information, p. 106 - 109 (2017/11/27)
A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in moderate to excellent yields.
Formation and direct detection of non-conjugated triplet 1,2-biradical from β,γ-vinylarylketone
Sriyarathne, H. Dushanee M.,Thenna-Hewa, Kosala R.S.,Scott, Tianeka,Gudmundsdottir, Anna D.
, p. 1707 - 1714 (2015/11/10)
Laser flash photolysis of 2-methyl-1-phenylbut-3-en-1-one (1) conducted at irradiation wavelengths of 266 and 308nm results in the formation of triplet 1,2-biradical 2 that has max at 370 and 480nm. Biradical 2 is formed with a rate constant of 1.1×107s-1 and decays with a rate constant of 2.3×105s-1. Isoprene-quenching studies support the notion that biradical 2 is formed by energy transfer from the triplet-excited state of the ketone chromophore of 1. Density functional theory calculations were used to verify the characterization of triplet biradical 2 and validate the mechanism for its formation. Thus, it has been demonstrated that intramolecular sensitization of simple alkenes can be used to form triplet 1,2-biradicals with the two radical centres localized on the adjacent carbon atoms.
Oxime-mediated oxychlorination and oxybromination of unactivated olefins
Dong, Kui-Yong,Qin, Hai-Tao,Liu, Feng,Zhu, Chen
supporting information, p. 1419 - 1422 (2015/03/04)
An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.
Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin
Dong, Kui-Yong,Qin, Hai-Tao,Bao, Xing-Xing,Liu, Feng,Zhu, Chen
supporting information, p. 5266 - 5268 (2015/01/09)
A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).
Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: Highly diastereoselective synthesis of trans-diamines from cycloalkenes
Zhu, Ming-Kui,Chen, Yu-Chen,Loh, Teck-Peng
supporting information, p. 5250 - 5254 (2013/05/23)
Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by me
Heteroaromatic synthesis via olefin cross-metathesis: Entry to polysubstituted pyridines
Donohoe, Timothy J.,Basutto, Jose A.,Bower, John F.,Rathi, Akshat
supporting information; experimental part, p. 1036 - 1039 (2011/04/27)
The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of α,β-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to mono-tetrasubstituted pyridines. Manipulation of the key 1,5-dicarbonyl intermediate allows access to pyridines with a wide range of substitution patterns. An extension of this methodology facilitates the preparation of pyridines embedded within macrocycles, as exemplified by an efficient synthesis of (R)-(+)-muscopyridine. High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology.(Figure Presented)
A new organic transformation by introducing crotyl/allyltrifluoroborates in cross-coupling reaction with aroyl chlorides
Al-Masum, Mohammad,Liu, Kwei-Yu
scheme or table, p. 5090 - 5093 (2011/10/19)
Microwave irradiated PdCl2(dtbpf) catalyzed direct cross-coupling reaction of aroyl chlorides with potassium crotyl/ allyltrifluoroborates has been developed. Regioselectivity of the cross-coupling product is varied from crotyltrifluoroborate to allyltrifluoroborate.
Iridium-Catalyzed coupling reaction of primary alcohols with 2-alkynes leading to hydroacylation products
Hatanaka, Shintaro,Obora, Yasushi,Ishii, Yasutaka
experimental part, p. 1883 - 1888 (2010/06/20)
A novel iridium-catalyzed intermolecular coupling reaction of primary alcohols or aldehydes with 2-alkynes was successfully achieved with high regioselectivity to give hydroacylation products such as α,β- unsaturated ketones in good yields. The mechanistic investigation of the reaction strongly indicated that the coupling proceeds through the initial formation of homoallylic alcohols followed by dehydrogenation to β,γ-unsatutated ketones and then isomerisation, which leads to the hydroacylation products.
