136185-86-9Relevant academic research and scientific papers
Recyclable polyisobutylene-supported pyridyl N-oxide allylation catalysts
Bergbreiter, David E.,Ortiz-Acosta, Denisse
, p. 5608 - 5610 (2008)
Polyisobutylene (PIB) is a useful soluble polymer support that facilitates catalyst recovery and recycling in liquid-liquid biphasic systems because the long polyisobutylene chain confers high phase selective solubility in the nonpolar phase of polar-nonpolar liquid-liquid biphasic systems on groups attached to the polymer's terminus. This work shows that PIB-supports that are effective with metal catalysts can also facilitate synthesis and use of organocatalysts. This is demonstrated by the use of a PIB-supported pyridyl N-oxide to promote the allylation of several aromatic aldehydes with allyltrichlorosilane. These studies show that a PIB-supported pyridyl N-oxide is a very active recyclable catalyst that promotes the allylation of aromatic aldehydes in yields of up to 99% yield. These PIB-supported pyridyl N-oxide catalysts were recovered in the hexane phase of a hexane/90% EtOH-H2O solvent system and were successfully recycled through 5 cycles with little effect on catalyst efficiency.
Highly efficient allylation of aldehydes promoted by maleic acid in aqueous media
Li, Gui-Long,Zhao, Gang
, p. 2540 - 2542 (2005)
A highly efficient promoter for allylation of aldehydes in aqueous media was developed. Under the promotion of maleic acid, the allylation of various aldehydes can be finished in a short period of reaction time to afford the corresponding homoallylic alco
o-Bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu4NF catalyst
Asao, Naoki,Shibato, Atsushi,Itagaki, Yoshifumi,Jourdan, Fabrice,Maruoka, Keiji
, p. 3177 - 3180 (1998)
A new type of fluoride ion catalyzed allylation agent, o- bis(allyldimethylsilyl)benzene (1a) and bis(allyldimethylsilyl)methane (1b), can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equili
Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes
Fu, Xiao-Yang,Si, Ya-Feng,Qiao, Li-Peng,Zhao, Yu-Fen,Chen, Xiao-Lan,Yu, Bing
supporting information, p. 574 - 580 (2021/11/13)
A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.
Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant
Fernandes, Rodney A.,Kumar, Praveen,Yadav, Sandhya S.
, p. 427 - 443 (2022/01/20)
This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(iii) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(iii) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.
Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton
Shikari, Amit,Mandal, Koushik,Chopra, Deepak,Pan, Subhas Chandra
supporting information, p. 58 - 63 (2021/11/09)
An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).
Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex
Gualandi, Andrea,Rodeghiero, Giacomo,Perciaccante, Rossana,Jansen, Thomas Paul,Moreno-Cabrerizo, Cristina,Foucher, Charles,Marchini, Marianna,Ceroni, Paola,Cozzi, Pier Giorgio
supporting information, p. 1105 - 1111 (2021/01/04)
The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2-phenylpyridine, 2 mol %), and N,N-diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. (Figure presented.).
Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates
Suzuki, Hiroyuki,Yamaguchi,Itoh, Akichika
, p. 1489 - 1494 (2020/12/13)
Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.
Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes
Shi, Caizhe,Li, Fusheng,Chen, Yuqing,Lin, Shuangjie,Hao, Erjun,Guo, Zhuowen,Wosqa, Urwa Tul,Zhang, Dandan,Shi, Lei
, p. 2992 - 2998 (2021/03/09)
The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.
Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions
Potenti, Simone,Gualandi, Andrea,Puggioli, Alessio,Fermi, Andrea,Bergamini, Giacomo,Cozzi, Pier Giorgio
supporting information, p. 1624 - 1627 (2021/02/05)
Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.
