7332-95-8Relevant academic research and scientific papers
Phosphorus(III)-Mediated, Tandem Deoxygenative Geminal Chlorofluorination of 1,2-Diketones
Choi, Garam,Chung, Won-Jin,Hwang, Sunjoo,Jang, Hanna,Kim, Ha Eun
, 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.
Visible light promoted continuous flow photocyclization of 1,2-diketones
Frongia, Angelo,Luridiana, Alberto,Porcu, Stefania,Ricci, Pier Carlo,Secci, Francesco
supporting information, p. 3684 - 3689 (2020/06/03)
The continuous flow Norrish-Yang photocyclization of 1,2-diketones has been developed and used for the synthesis of a large number of functionalized 2-hydroxycyclobutanones, under blue light irradiation and employing acetone as a solvent. This eco-friendly procedure represents a valid alternative to the reactions carried out in batches thus reducing the reaction times, the formation of secondary products and simplifying the purification steps. The use of differently substituted diketone compounds has allowed us to obtain a wide range of 2 and 3-functionalized cyclobutanones, thus allowing the evaluation of the scope and limitations of this procedure.
A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones
Miles, Dillon H.,Guasch, Joan,Toste, F. Dean
, p. 7632 - 7635 (2015/07/02)
The enantioselective addition of anilines to azoalkenes was accomplished through the use of a chiral phosphoric acid catalyst. The resulting α-arylamino hydrazones were obtained in good yields and excellent enantioselectivities and provide access to enantioenriched α-arylamino ketones. A serendipitous kinetic resolution of racemic α-arylamino hydrazones is also described.
Catalytic oxidation of silyl enol ethers to 1,2-diketones employing nitroxyl radicals
Hayashi, Masaki,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
, p. 1025 - 1030 (2012/06/04)
A novel and efficient method for the preparation of 1,2-diketones is reported. A series of -diketones were readily prepared by the nitroxyl-radical-catalyzed oxidation of silyl enol ethers using magnesium monoperoxyphthalate hexahydrate (MMPP6H) as the co-oxidant. Georg Thieme Verlag Stuttgart · New York.
Palladium-catalyzed carbonation-diketonization of terminal aromatic alkenes via carbon-nitrogen bond cleavage for the synthesis of 1,2-diketones
Wang, Azhong,Jiang, Huanfeng,Li, Xianwei
supporting information; experimental part, p. 6958 - 6961 (2011/10/02)
A palladium-catalyzed carbonation-diketonization reaction of terminal alkenes via carbon-nitrogen bond cleavage under an atmosphere of oxygen has been developed. A series of 1,2-diketones were readily prepared from the reaction of aromatic terminal alkenes with nitroalkanes.
Enantioselective aerobic oxidation of α-hydroxy-ketones catalyzed by oxidovanadium(V) methoxides bearing chiral, N-salicylidene- tert -butylglycinates
Chen, Chien-Tien,Kao, Jun-Qi,Salunke, Santosh B.,Lin, Ya-Hui
, p. 26 - 29 (2011/03/22)
Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N- salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (krel).
Oxidation of alkynes in aqueous media catalyzed by diphenyl diselenide
Santoro, Stefano,Battistelli, Benedetta,Gjoka, Blerina,Si, Chun-Wing Steven,Testaferri, Lorenzo,Tiecco, Marcello,Santi, Claudio
scheme or table, p. 1402 - 1406 (2010/07/14)
In this communication we propose a convenient methodology to effect the oxidation of alkynes using ammonium persulfate and diphenyl diselenide as catalyst. The reactions effected in aqueous media lead to 1,2-unprotected dicarbonyl derivatives or to hemiacetals starting from terminal alkynes.
Gold(I)-catalyzed oxidative rearrangements
Witham, Cole A.,Mauleon, Pablo,Shapiro, Nathan D.,Sherry, Benjamin D.,Toste, F. Dean
, p. 5838 - 5839 (2008/02/12)
A series of gold(I)-catalyzed oxidative rearrangement reactions of alkynes using sulfoxides as stoichiometric oxidants are reported. The reactions are postulated to proceed through intermolecular oxygen atom transfer from the sulfoxide to gold(I)-carbenoi
A Highly Efficient Ruthenium-Catalyzed Rearrangement of α,β-Epoxyketones to 1,2-Diketones
Chang, Chia-Lung,Kumar, Manyam Praveen,Liu, Rai-Shung
, p. 2793 - 2796 (2007/10/03)
TpRuPPh3(CH3CN)2PF6 catalyzed the efficient rearrangement of α,β-epoxyketones to 1,2-diketones. Unlike a previously reported iron catalyst, the reaction in this case is applicable not only to 1,2-disubstituted epoxides but also to mono- and trisubstituted epoxides and tolerates oxygen functionalities. The sterically crowded and highly basic tris(1-pyrazolyl)borate (Tp) ligand of the ruthenium catalyst might account for its high selectivity toward 1,2-diketone rather than 1,3-diketone.
Chemistry of singlet oxygen. Dye-sensitized photooxygenation of arylallenes
Erden,Martinez
, p. 1859 - 1862 (2007/10/02)
1-Arylallenes react with singlet oxygen via 1,2-and 1,4-cycloaddition modes giving rise to three types of carbonyl fragments. 1,1-Diphenyl- and 1-phenylallenes react predominantly by the 1,4-mode. Plausible mechanisms are discussed for the formation of the observed products.
