34650-69-6Relevant academic research and scientific papers
One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst
Song, Tao,Zhou, Xin,Wang, Xiaoxue,Xiao, Jianliang,Yang, Yong
supporting information, p. 1955 - 1959 (2021/03/26)
A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.
Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2-Alkynyl Carbonyls to 1,2-Dicarbonyls
Hu, Ming,Li, Jin-Heng,Li, Yang,Lu, Yuan,Luo, Mu-Jia
supporting information, (2020/05/01)
A tandem transformation of 2-alkynyl carbonyl compounds by means of a CuBr2/I2/DMSO/water system is developed, enabling the fromation of various functionalized 1,2-dicarbonyl compounds, including 1,2-diketones, α-keto amides and α-keto ester. This Cu-promoted iodine-mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C?C bond cleavage cascades. (Figure presented.).
Palladium-Catalyzed Oxidative C≡C Triple Bond Cleavage of 2-Alkynyl Carbonyl Compounds Toward 1,2-Dicarbonyl Compounds?
Hu, Ming,Li, Jin-Heng,Luo, Mu-Jia,Zhou, Ming-Bo
, p. 553 - 558 (2020/04/20)
A new, general palladium-catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2-alkynyl carbonyl compounds, including 1,3-disubstituted prop-2-yn-1-ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2-dicarbonyl compounds, e.g., 1,2-diones, 2-keto amides and 2-keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.
Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds
Chen, Li-Sha,Zhang, Lu-Bing,Tian, Yue,Li, Jin-Heng,Liu, Yong-Quan
supporting information, p. 5523 - 5526 (2020/09/02)
A new, general oxidative route to transformations of 1,3-dicarbonyl compounds to 1,2-dicarbonyl compounds by merging copper and I2 catalysis is described. This method is applicable to broad 1,3-dicarbonyl compounds, including 1,3-diketones, 1,3-keto esters and 1,3-keto amides. Mechanistical studies show that the reaction is achieved via the C–C bond cleavage and CO release cascades.
Phosphorus(III)-Mediated, Tandem Deoxygenative Geminal Chlorofluorination of 1,2-Diketones
Choi, Garam,Chung, Won-Jin,Hwang, Sunjoo,Jang, Hanna,Kim, Ha Eun
supporting information, p. 4190 - 4195 (2020/06/27)
Tetrasubstituted carbon containing two different halogen substituents was constructed in a single-step operation by utilizing the carbene-like reactivity of dioxaphospholene through the tandem reaction of electrophilic and nucleophilic halogenating reagents. It was crucial to devise non-dealkylatable phosphoramidite, which enabled the efficient formation of geminal chlorofluorides from various 1,2-diketones with (PhSO2)2NF and n-Bu4NCl. In addition, selective functionalization of the chlorine substituent was demonstrated, and the absence of halogen scrambling was confirmed.
A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
Ma, Zhiming,Ren, Peng,Song, Tao,Xiao, Jianliang,Yang, Yong,Yuan, Youzhu
, p. 4617 - 4629 (2020/05/19)
We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.
Metal-Free [4+2] Annulation of Arylalkynes with tert-Butyl Nitrite through C(sp2)-H Oxidation to Assemble Benzo[e][1,2]oxazin-4-ones
Yang, Xu-Heng,Song, Ren-Jie,Li, Jin-Heng
supporting information, p. 3849 - 3856 (2016/01/25)
A metal-free radical-mediated [4+2] annulation of internal arylalkynes with tert-butyl nitrite (t-BuONO) is presented for the synthesis of benzo[e][1,2]oxazin-4-ones through the addition of t-BuONO across the C-C triple bond, hydration, isomerization and aromatic C(sp2)-H oxidation cascades. The 18O-labeling experiment shows that two oxygen atoms in the product system are from water.
A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes
Chen, Hongyi,Zhang, Liming
supporting information, p. 11775 - 11779 (2015/10/05)
Donor-substituted acyl gold carbenes are challenging to access selectively by gold-promoted intermolecular oxidation of internal alkynes as the opposite regioisomers frequently predominate. By using alkynyl sulfones or sulfonates as substrates, the oxidative gold catalysis in the presence of substituted pyridine N-oxides offers regiospecific access to acyl/aryl, acyl/alkenyl, and acyl/alkoxy gold carbenes by in situ expulsion of sulfur dioxide. The intermediacies of these reactive species are established by their reactivities, including undergoing further oxidation by the same oxidant, cyclopropanation of styrenes, engaging in a [3+2] cycloaddition with α-methylstyrene, and conversion into dienones. Accept it: A desulfonylative approach was developed to regiospecifically access these underexplored acyl gold carbenes from either alkynyl aryl/alkenyl sulfones or alkynyl sulfonate substrates. The reactivities of these donor- and acceptor-substituted carbenes are examined.
