72012-45-4Relevant academic research and scientific papers
Synthesis of Enantioenriched α,α-Difluoro-β-arylbutanoic Esters by Pd-Catalyzed Asymmetric Hydrogenation
Dong, Kaiwu,Feng, Sitian,Shen, Chaoren,Tang, Yitian,Yang, Chenjue
supporting information, p. 7508 - 7512 (2020/10/09)
Synthesis of optically active gem-difluorinated organic molecules attracts a great deal of interest due to their unique properties in pharmaceutical and agrochemical areas. Herein, a series of enantioenriched α,α-difluoro-β-arylbutanoic esters were prepar
Domino Aryne Annulation via a Nucleophilic-Ene Process
Xu, Hai,He, Jia,Shi, Jiarong,Tan, Liang,Qiu, Dachuan,Luo, Xiaohua,Li, Yang
supporting information, p. 3555 - 3559 (2018/03/21)
1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.
Hypervalent iodine(III)-Mediated oxidative decarboxylation of β,γ-unsaturated carboxylic acids
Kiyokawa, Kensuke,Yahata, Shunsuke,Kojima, Takumi,Minakata, Satoshi
supporting information, p. 4646 - 4649 (2015/01/09)
A novel oxidative decarboxylation of β,γ-unsaturated carboxylic acids mediated by hypervalent iodine(III) reagents is described. The decarboxylative C-O bond forming reaction proceeded in the presence of PhI(OAc)2 to give the corresponding allylic acetates. In addition, decarboxylative C-N bond formation was achieved by utilizing hypervalent iodine(III) reagents containing an I-N bond. Mechanistic studies suggest the unique reactivity of hypervalent iodine reagents in this ionic oxidative decarboxylation.
A novel ketone olefination via organozinc reagents in the presence of diphenyl phosphite
Cui, Hua,Li, Ying,Zhang, Songlin
supporting information, p. 2862 - 2869 (2012/11/07)
Carbonyl compounds react with organozinc reagents in the presence of diphenyl phosphite to give the corresponding olefins. A variety of 1,3-dienes and unsaturated esters were obtained in moderate to excellent yields under mild conditions. The Royal Society of Chemistry 2012.
Intramolecular Photoaddition of Secondary α-(Aminoalkyl)styrenes
Lewis, Frederick D.,Bassani, Dario M.,Reddy, G. Dasharatha
, p. 6390 - 6393 (2007/10/02)
The photophysical and photochemical behavior of a series of α-styrenes with two to four methylenes separating the styryl and amino groups and an (aminoalkyl)indene have been investigated and the results compared to those for the intermolecular reaction of α-methylstyrene with diethylamine.Both inter- and intramolecular quenching of styrene fluorescence by the amine is observed, indicative of electron-transfer quenching as the initial step in these reactions.The resulting exciplex undergoes regioselective N-H proton transfer to styrene C-βyielding a biradical, in the case of the intramolecular reaction, and a radical pair, in the case of the intermolecular reaction.Biradical or radical pair combination yields styrene-amine addition products.The conformation of the intermediate exciplex is proposed to control the regioselectivity of the intramolecular N-H proton transfer process.
Steric and Electronic Effects on the Photochemical Reactivity of Oxime Acetates of β,γ-Unsaturated Aldehydes
Armesto, Diego,Horspool, William M.,Gallego, Mar G.,Agarrabeitia, Antonia R.
, p. 163 - 170 (2007/10/02)
A general synthesis of 5-unsubstituted N-acetoxy 3,3-dimethyl-1-azapenta-1,4-dienes starting from 2-(1,3-dithian-2-yl)-2-methylpropanal is described.The influence of 5-phenyl, 4-phenyl, 5-cyclohexyl, 5-tert-butoxycarbonyl and 5,5-dicyclohexyl substitution on the outcome of the photochemical reactions of the oxime acetates of β,γ-unsaturated aldehydes has been studied with a view to proving or disproving the operation of a deactivating free rotor in the aza-di-?-methane rearrangement.The results obtained show that if the radical formed at C-5 can be stabilized by conjugation with an aryl group or by certain types of disubstitution then the aza-di-?-methane rearrangement takes place successfully.In any other situation the reaction fails.These results clearly show that the free rotor effect is not responsible for the failure of C-5 monosubstituted 1-aza-1,4-dienes to undergo the aza-di-?-methane rearrangement.
