47074-06-6Relevant articles and documents
Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium ylides and cyclopropanols for δ-diketone synthesis
Fan, Shuaixin,Fang, Lili,Li, Tielei,Wu, Weiping,Zhu, Jin
supporting information, p. 7386 - 7389 (2021/08/03)
Previous transition metal-catalyzed synthesis processes of δ-diketones are plagued by the high cost of the rhodium catalyst and harsh reaction conditions. Herein a low-cost, room temperature ruthenium catalytic method is developed based on the coupling of α-keto sulfoxonium ylides with cyclopropanols. The mild protocol features a broad substrate scope (47 examples) and a high product yield (up to 99%). Mechanistic studies argue against a radical pathway and support a cyclopropanol ring opening, sulfoxonium ylide-derived carbenoid formation, migratory insertion C-C bond formation pathway.
Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones
Samser, Shaikh,Biswal, Priyabrata,Meher, Sushanta Kumar,Venkatasubbaiah, Krishnan
, p. 1386 - 1394 (2021/02/27)
One-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol result in the formation of 1,5-diketone products. This simple one-pot method avoids the use of highly electrophilic vinyl ketones.
Photo-mediated [1, 3]-Carbonyl shift of β-Ketocarbonyls
Zhang, Wenzhao,Li, Yao,Luo, Sanzhong
, (2020/04/29)
An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible light irradiation. This photolytic protocol provides an alternative approach to the synthesis of 1,5-dicarbonyl compounds. By chiral primary amine catalysis, a kinetic resolution was also developed to afford enantioenriched 1,5-dicarbonyls.
Palladium-catalyzed cross-coupling of styrenes with aryl methyl ketones in ionic liquids: Direct access to cyclopropanes
Cotugno, Pietro,Monopoli, Antonio,Ciminale, Francesco,Milella, Antonella,Nacci, Angelo
supporting information, p. 13563 - 13567 (2015/01/09)
The combined use of Pd(OAc)2, Cu(OAc)2, and dioxygen in molten tetrabutylammonium acetate (TBAA) promotes an unusual cyclopropanation reaction between aryl methyl ketones and styrenes. The process is a dehydrogenative cyclizing coupl
Generation of β-keto radicals from cyclopropanols catalyzed by AgNO3
Chiba, Shunsuke,Cao, Zhengyan,El Bialy, Serry Atta Atta,Narasaka, Koichi
, p. 18 - 19 (2007/10/03)
Various β-keto radicals are generated from cyclopropanols by treatment with a catalytic amount of AgNO3 and (NH4) 2S2O8 as a reoxidant in the presence of pyridine. Thus, generated β-keto radicals react with alkenes to yield addition products. Copyright
Generation of β-Carbonyl Radicals from Cyclopropanol Derivatives by the Oxidation with Manganese(III) 2-Pyridinecarboxylate and Their Reactions with Electron-Rich and -Deficient Olefins
Iwasawa, Nobuharu,Hayakawa, Satoshi,Funahashi, Masahiro,Isobe, Koichi,Narasaka, Koichi
, p. 819 - 827 (2007/10/02)
Various β-carbonyl radicals are generated oxidatively from cyclopropanol derivatives by the use of manganese(III) 2-pyridinecarboxylate (Mn(pic)3).These β-carbonyl radicals react with electron-rich olefins such as conjugated silyl enol ethers, a ketene th
α-arylation vs. α-arylhydrazonylation of alkyl aryl ketones with arylazo tert-butyl sulfides
Dell'Erba,Novi,Petrillo,Tavani
, p. 235 - 242 (2007/10/02)
Potassium enolates of alkyl aryl ketones react selectively in DMSO with phenylazo 1a and 4-methylphenylazo tert-butyl sulfide 1b undergoing respectively effective α-phenylation via S(RN)1 and α-(4-methylphenyl)hydrazonylation via elimination-addition.
Generation of β-Keto Radicals from Cyclopropanol Derivatives by the Use of Manganese(III) 2-Pyridinecarboxylate as an Oxidant and Their Reactions with Olefins
Iwasawa, Nobuharu,Hayakawa, Satoshi,Isobe, Koichi,Narasaka, Koichi
, p. 1193 - 1196 (2007/10/02)
Various β-keto radicals are generated from cyclopropanol derivates such as 1- or 2-substituted cyclopropanols and a cyclopropanone hemiacetal by the use of manganese(III) 2-pyridinecarboxylate, and their reactions with electron-rich olefins give cross-addition products in good yields.
Carbanions That Function Both as Electron Transfer Agents and as Hydrogen Atom Donors: A New Electron Transfer Chain Reaction
Kornblum, Nathan,Chen, S. I.,Kelly, William J.
, p. 1830 - 1831 (2007/10/02)
New reactions are described in which carbanions function both as one electron transfer agents and as hydrogen atom donors; a novel feature of these reactions is the generation of a radical anion by hydrogen atom abstraction.
Enaminone Intermediate in the One-Methylene Incorporated Dimerization Reaction of Ketone Enolate. Cross Reaction to Unsymmetrical 1,5-Diketones
Kiyooka, Syun-ichi,Yamashita, Tsuneo
, p. 1775 - 1778 (2007/10/02)
An enaminone has been isolated as an intermediate from the one-methylene incorporated dimerization reaction of ketone enolate using N-phenyl-N-methylformamide.The reaction of the enaminone with the other ketone enolates gives unsymmetrical 1,5-diketones i