32097-05-5Relevant academic research and scientific papers
Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones
Gao, Pan-Pan,Yan, Dong-Mei,Bi, Ming-Hang,Jiang, Min,Xiao, Wen-Jing,Chen, Jia-Rong
supporting information, p. 14195 - 14201 (2021/09/20)
A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.
Cross-coupling of meyer-schuster intermediates under dual gold-photoredox catalysis
Um, Jiwon,Yun, Hokeun,Shin, Seunghoon
, p. 484 - 487 (2016/02/18)
Under dual gold/photoredox catalytic conditions, intermediates from the Meyer-Schuster rearrangement underwent an efficient cross-coupling with arene diazonium salts, leading to α-arylated enones. Diazonium salts assisted the dissociation of the propargyl
One-step synthesis of indanones through NbCl5-induced Friedel-Crafts reaction
Da Silva Barbosa, Jader,Da Silva, Gil Valdo José,Constantino, Mauricio Gomes
, p. 4649 - 4652 (2015/08/06)
Abstract This Letter describes the use of NbCl5 as the Lewis acid in Friedel-Crafts reactions, in which a bifunctional electrophile reacts inter- and intramolecularly with an aromatic ring to produce a number of indanones in a single step, main
Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement and 1,4-addition to the resulting vinyl ketone
Okamoto, Noriko,Sueda, Takuya,Yanada, Reiko
, p. 9854 - 9859 (2015/01/16)
Bi(OTf)3-catalyzed Meyer-Schuster rearrangement of electron-rich propargyl alcohols, followed by 1,4-addition of the resulting vinyl ketone, proceeded smoothly though Meyer-Schuster rearrangement of primary propargyl alcohols is rare. This tandem reaction can be extended to an intramolecular version, featuring a one-pot dihydroquinolone synthesis. (Chemical Equation Presented).
p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles
Jacubert, Maud,Provot, Olivier,Peyrat, Jean-Fran?ois,Hamze, Abdallah,Brion, Jean-Daniel,Alami, Mouad
experimental part, p. 3775 - 3787 (2010/07/04)
Regioselective hydration of a wide range of internal alkynes has been afforded in high to good yields by using PTSA in EtOH. The scope of the reaction of alkynes has been delineated. Arylaliphatic alkynes and diarylalkynes were regioselectively hydrated in good to excellent yields and short reaction times when the reaction was achieved under microwave irradiation. Moreover, diarylalkynes, arylenynes as well as diaryldiynes bearing a methoxy- or a thiomethyl substituent on the ortho position underwent a regioselective 5-endo-dig-cyclization to give a variety of 2-aryl- and 2-styrylbenzofuran or benzothiphene derivatives. We believe that, this new environmentally metal-free procedure combined to microwave irradiation would be in importance in the search of green laboratory-scale synthesis.
Platinum-catalyzed addition of dimethylsilylene to β-methyl α-β-unsaturated ketones: γ-silylation forming 1-Oxa-2-silacyclohex-5-enes
Okamoto, Kazuhiro,Hayashi, Tamio
, p. 5067 - 5069 (2008/03/27)
The reaction of β-methyl α,β-unsaturated ketones with pentamethyldisilane in the presence of a platinum catalyst brought about silylation on the β-methyl group giving high yields of oxasilacyclohexenes.
Highly efficient p-toluenesulfonic acid-catalyzed alcohol addition or hydration of unsymmetrical arylalkynes
Olivi, Nathana?l,Thomas, Emmanuel,Peyrat, Jean-Fran?ois,Alami, Mouad,Brion, Jean-Daniel
, p. 2175 - 2179 (2007/10/03)
Under a catalytic amount of PTSA in aqueous or alcoholic media, activated unsymmetrical arylalkynes 1 undergo regioselective water or alcohol addition to afford successfully carbonyl compounds 2 in good to excellent yields. This new environmentally metal-free procedure, which afforded only Markovnikov adducts, is characterized by the mildness of acidic conditions and the excellent regio- and chemoselectivity.
A new and one-pot synthesis of α,β-unsaturated ketones by dehydrogenation of various ketones with n-tert-butyl phenylsulfinimidoyl chloride
Mukaiyama, Teruaki,Matsuo, Jun-Ichi,Kitagawa, Hideo
, p. 1250 - 1251 (2007/10/03)
α,β-Unsaturated ketones were synthesized by one-pot procedure from various ketones in good to excellent yields on treatment of their lithium enolates with N-tert-butyl phenylsulfinimidoyl chloride (1) under mild conditions.
Metal-Metal Exchange of α-Metallo Ketones. Novel Formation of α-Acyl Anion and α-Keto Carbonium Ion Equivalents from (Aryl)phenacyl TlIII, PbIV, and HgII Systems
Moriarty, Robert M.,Penmasta, Raju,Prakash, Indra,Awasthi, Alok K.
, p. 1022 - 1025 (2007/10/02)
The novel class of α-metallo ketones RCOCH2TlIIItolyl(OCOCF3) where R = phenyl, substituted phenyl, thienyl, pyridinyl, and tert-butyl have been synthesized and characterized by 1H NMR and 13C NMR.These compounds serve as anion equivalents in the TiCl4-mediated aldol condensation.Metal-metal exchange with iodosylbenzene or lead tetraacetate leads to α-nucleophilic substitution derived from the formal α-keto carbonium ion equivalent.The corresponding p-CH3OC6H4COCH2PbIVC6H4OCH3-p-(OCOCH3)2 and (p-CH3OC6H4COCH2)2HgII analogues were synthesized and shown to likewise behave as either enolate anion or α-keto carbonium ion equivalents upon metal-metal exchange with TiIV, PbIV, or IIII.The importance of this work is that the range of reactivity of α-metallo ketones may be selectively adjusted by metal-metal or metal-metalloid exchange.
