65622-33-5Relevant academic research and scientific papers
Synthesis of 2,5,8,11,14,17-hexafluoro-hexa-peri-hexabenzocoronene for n-type organic field-effect transistors
Kikuzawa, Yoshihiro,Mori, Tomohiko,Takeuchi, Hisato
, p. 4817 - 4820 (2007)
(Chemical Equation Presented) A fluorine-substituted hexa-peri- hexabenzocoronene was synthesized as a thermostable active material for n-type semiconductors. The LUMO and HOMO energy levels, estimated by UV-vis and photoelectron spectroscopy, were lower
Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone
Yao, Liangliang,Hu, Qiong,Bao, Li,Zhu, Wenjing,Hu, Yimin
supporting information, p. 4971 - 4975 (2021/06/30)
An unprecedented C═C double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.
Iron-Catalyzed One-Step Synthesis of Isothiazolone/1,2-Selenazolone Derivatives via [3+1+1] Annulation of Cyclopropenones, Anilines, and Elemental Chalcogens
Wang, Hongchen,Yan, Rulong
supporting information, (2021/12/22)
Described herein is the one-step synthesis of isothiazolone/1,2-selenazolone derivatives via [3+1+1] cycloaddition of cyclopropenone derivatives, anilines, and elemental chalcogens. The cascade reaction involves the C?S, C?N, and N?S bond formation along with the cleavage of C?C bond. Both anilines and cyclopropenones are tolerated and give the corresponding products in 28–73% yields. (Figure presented.).
Lanthanide Silylamide-Catalyzed Synthesis of Pyrano[2,3- b]indol-2-ones
Chen, Qifa,Teng, Yue,Xu, Fan
supporting information, p. 4785 - 4790 (2021/06/28)
A lanthanide silylamide-catalyzed tandem reaction of isatins, diethyl phosphite, and 2,3-diarylcyclopropenones has been developed. A series of pyrano[2,3-b]indol-2-ones were synthesized in high yields. The cooperation of the Lewis acidity of the lanthanide center and the Bronsted basicity of the N(SiMe3)2 anion may be the key factor affecting the catalytic activity of lanthanide amides.
Catalytic Asymmetric (3 + 3) Cycloaddition of Oxyallyl Zwitterions with α-Diazomethylphosphonates
Liu, Yan,Peng, Xian,Peng, Yungui,She, Rui,Zhou, Xin
supporting information, p. 7295 - 7300 (2021/10/01)
The unique structure of oxyallyls represents a significant challenge for their catalytic asymmetric applications. Herein, an unprecedented chiral imidodiphosphoric acid-catalytic enantioselective (3 + 3) cycloaddition between oxyallyl zwitterions generate
Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles
Gao, Wen-Xia,Huang, Xiao-Bo,Liu, Miao-Chang,Miao, Wei-Hang,Wu, Hua-Yue,Zhou, Yun-Bing
supporting information, p. 9425 - 9430 (2021/12/14)
Represented is a CuX2- or I2-promoted ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, providing an efficient method for the synthesis of 3-haloacrylates. The ring-opening reaction enables the construction of two C–X (X = Cl, Br, or I) bonds and a C–O bond as well as the cleavage of two C–O bonds and a C–C bond in a single step. This protocol is highly atom economical, has an excellent substrate scope, and exhibits the ability for gram-scale reaction.
From Alkyl Halides to Ketones: Nickel-Catalyzed Reductive Carbonylation Utilizing Ethyl Chloroformate as the Carbonyl Source
Shi, Renyi,Hu, Xile
supporting information, p. 7454 - 7458 (2019/04/30)
Ketones are an important class of molecules in synthetic and medicinal chemistry. Rapid and modular synthesis of ketones remains in high demand. Described here is a nickel-catalyzed three-component reductive carbonylation method for the synthesis of dialkyl ketones. A wide range of both symmetric and asymmetric dialkyl ketones can be accessed from alkyl halides and a safe CO source, ethyl chloroformate. The approach offers complementary substrate scope to existing carbonylation methods while avoiding the use of either toxic CO or metal carbonyl reagents.
Organocatalytic Regiodivergent C?C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks
Cao, Jian,Fang, Ran,Liu, Jin-Yu,Lu, Hong,Luo, Yong-Chun,Xu, Peng-Fei
supporting information, p. 18863 - 18867 (2018/11/23)
Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain-release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen-bonding network activation and a regiodivergent strain-assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a “spring-loaded” intermediate with switchable C?C bond cleavages achieved by controllable ring-strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.
Generation and Reactivity Studies of Diarylmethyl Radical Pairs in Crystalline Tetraarylacetones via Laser Flash Photolysis Using Nanocrystalline Suspensions
Park, Jin H.,Hughs, Melissa,Chung, Tim S.,Ayitou, A. Jean-Luc,Breslin, Vanessa M.,Garcia-Garibay, Miguel A.
supporting information, p. 13312 - 13317 (2017/10/05)
The nanosecond electronic spectra and kinetics of the radical pairs from various crystalline tetraarylacetones were obtained using transmission laser flash photolysis methods by taking advantage of aqueous nanocrystalline suspensions in the presence of su
Organocatalyzed [3 + 2] Annulation of Cyclopropenones and β-Ketoesters: An Approach to Substituted Butenolides with a Quaternary Center
Li, Xuanyi,Han, Chunhua,Yao, Hequan,Lin, Aijun
supporting information, p. 778 - 781 (2017/03/01)
An unprecedented organocatalyzed [3 + 2] annulation of cyclopropenones and β-ketoesters has been developed. This reaction provides a direct approach to highly substituted butenolides with a quaternary center in moderate to good yields. The preliminary mechanism study verified that the enol intermediate is crucial to the reaction outcome and the intermolecular esterification and intramolecular Michael addition process were involved.
