3677-70-1Relevant academic research and scientific papers
Method for synthesizing alkyl olefin through coupling of double-bond carbon-hydrogen bond and saturated carbon-hydrogen bond
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Paragraph 0070-0073; 0097, (2021/02/10)
The invention discloses a method for synthesizing alkyl olefin through coupling of a double-bond carbon-hydrogen bond and a saturated carbon-hydrogen bond. According to to the method, one-pot reactionis implemented on olefin and sulfoxide in the presence of ferric salt and hydrogen peroxide to generate alkyl olefin; in the method, sulfoxide is simultaneously used as a hydrocarbylation reagent anda solvent of olefin, and a reaction product is alkyl olefin from sulfoxide alkyl coupled with olefin carbon atoms, so that an olefin carbon chain is increased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.
Method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins
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Paragraph 0054-0063; 0082-0084, (2021/02/06)
The invention discloses a method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins, wherein the method comprises the steps: carrying out hydrocarbylation reaction on the non-terminal olefins and sulfoxide in the presence of ferric salt and hydrogen peroxide, carrying out one-pot reaction on disubstituted non-terminal olefins to generate the trisubstituted olefins, and carrying out one-pot reaction on the trisubstituted non-terminal olefins to generate the tetrasubstituted olefins. In the method, sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefins, and one more hydrocarbyl substituent is added to a reaction product compared with a double-bond carbon atom of a reactant, so that an olefin carbon chain isincreased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.
Triphenylethylene multifunctional photoresponse compound as well as preparation method and application thereof
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Paragraph 0066-0072, (2021/11/06)
The invention provides a triphenylethylene multifunctional photoresponse compound. The structural formula of the triphenylethylene multifunctional photoresponse compound is as shown in formula 1, and in the formula 1, R1 and R2 are respectively and independently selected from one of bromine and hydrogen, and X is methyl or substituted methyl. The compound is a triphenylethylene pure organic room-temperature phosphorescent material, has the properties of photochromism, photodeformation, room-temperature phosphorescence and the like, and can be used in multiple fields of preparation of anti-counterfeiting marks, preparation of micro machinery and the like. The invention also provides a preparation method of the triphenylethylene multifunctional photoresponse compound. The preparation method has the advantages of cheap and easily available raw materials, few synthesis steps, simple preparation and mild reaction conditions, and is suitable for large-scale production. The invention further provides application of the triphenylethylene multifunctional photoresponse compound in preparation of an anti-counterfeiting mark and manufacturing of a micro machine.
Microwave-assisted periselective annulation of triarylphosphenes with aldehydes and ketones
Du, Changle,Fu, Xingyang,Fu, Zhicheng,Luo, Yun,Xu, Jiaxi
, p. 9526 - 9537 (2020/12/15)
The reaction of diazo(aryl)methyl(diaryl)phosphine oxides with aldehydes and ketones generates benzo-δ-phosphinolactones in low to good yields with 1,1-diarylalk-1-enes as byproducts under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo a Wolff rearrangement to form diaryl(aryl)phosphenes, which further react with aldehydes and ketones to afford benzo-δ-phosphinolactones and β-phosphinolactones. The latter are unstable under heating and fragment into the corresponding 1,1-diarylalk-1-enes and arylphosphine dioxides under reaction conditions. The arylphosphine dioxides become arylphosphonic acids during workup. The periselectivity in the annulation shows that the reaction of diaryl(aryl)phosphenes with most aldehydes and ketones favors phosphene phenyl participation in (4 + 2) annulation(2 + 2) annulation. This journal is
Oxidative heck arylation for the stereoselective synthesis of tetrasubstituted olefins using nitroxides as oxidants
He, Zhiheng,Kirchberg, Sylvia,Froehlich, Roland,Studer, Armido
, p. 3699 - 3702 (2012/05/20)
One, two, and three! Nitroxides and dioxygen serve as oxidants in highly stereoselective oxidative Pd-catalyzed Heck arylations in which aryl boronic acids are used to synthesize triarylalkyl-substituted olefins. The reactions occur under very mild conditions at room temperature. As an example, the threefold sequential arylation of methyl acrylate is the crucial step in the stereoselective synthesis of Z-Tamoxifen.
A one-pot cross-pinacol coupling/rearrangement procedure
Scheffler, Ulf,Mahrwald, Rainer
, p. 1970 - 1975,6 (2012/12/12)
A new catalytic retro-pinacol/cross-pinacol reaction, followed by subsequent rearrangement or deoxygenation of the intermediately formed vicinal diols, is described. This operationally simple one-pot protocol allows isolation of geminal α,α-diphenyl ketones or 1,1-diphenyl alkenes with high yields and selectivities. Copyright
A versatile palladium catalyst system for Suzuki-Miyaura coupling of alkenyl tosylates and mesylates
Wong, Pui Yu,Chow, Wing Kin,Chung, Kin Ho,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
supporting information; experimental part, p. 8328 - 8330 (2011/09/14)
A general and effective palladium system for Suzuki-Miyaura coupling of alkenyl electrophiles under mild reaction conditions is reported. With the Pd(OAc)2/CM-phos system, a variety of alkenyl tosylates are coupled well with ArB(OH)2. Moreover, the first successful examples of using alkenyl mesylates in alkenylation are also described.
Well-defined air-stable palladium HASPO complexes for efficient Kumada-Corriu cross-couplings of (Hetero)aryl or alkenyl tosylates
Ackermann, Lutz,Kapdi, Anant R.,Fenner, Sabine,Kornhaab, Christoph,Schulzke, Carola
supporting information; experimental part, p. 2965 - 2971 (2011/05/05)
Palladium complexes of representative heteroatom-substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X-ray crystal structure analysis. Importantly, these well-defined complexes served as highly efficient catalysts for Kumada-Corriu cross-coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air-stable catalyst derived from inexpensive PinP(O)H displayed a remarkably high catalytic efficacy, which resulted in cross-couplings at low catalyst loadings under exceedingly mild reaction conditions with ample scope.
Insights into the general and efficient cross McMurry reactions between ketones
Duan, Xin-Fang,Zeng, Jing,Lue, Jia-Wei,Zhang, Zhan-Bin
, p. 9873 - 9876 (2007/10/03)
The selective cross McMurry couplings of diaryl or aryl ketones with various substituted ketones were achieved in 53-94% isolated yields. It is believed that the strong affinity of the substituents to the low-valent titanium surface plays an important role in regards to moderating selectivity. Through the introduction of such substituents followed by their removal post McMurry coupling, structurally similar ketones can be effectively cross-coupled.
Regio- and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids
Zhou, Chengxiang,Larock, Richard C.
, p. 3765 - 3777 (2007/10/03)
The Pd-catalyzed three-component coupling of readily available aryl iodides, internal alkynes, and arylboronic acids provides a convenient, one-step, regio- and stereoselective route to tetrasubstituted olefins in good to excellent yields, although electron-poor aryl iodides and dialkylalkynes normally afford only low yields under our standard reaction conditions. The proper combination of substrates and reaction conditions is important for high yields. The presence of water generally substantially increases the yields of the desired tetrasubstituted olefins. The reaction involves cis-addition of the aryl group from the aryl iodide to the less hindered or more electron-rich end of the alkyne, while the aryl group from the arylboronic acid adds to the other end. A modified, room-temperature procedure has also been successfully developed, which works very well for some substrates. Tamoxifen and its derivatives are synthesized in a concise, regio- and stereoselective manner by applying our synthetic protocol.
