95929-64-9Relevant academic research and scientific papers
Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile
Tsuji, Hiroaki,Hashimoto, Keisuke,Kawatsura, Motoi
, p. 8837 - 8841 (2019/11/11)
The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.
Palladium catalyzed direct benzylation/allylation of malonates with alcohols-: In situ C-O bond activation
Cao, Xueqin,Zhang, Yugen
supporting information, p. 2638 - 2641 (2016/05/24)
High step- and atom-economy are the endlessly pursued in organic and pharmaceutical syntheses. Herein, a new method for directly coupling benzyl/allyl alcohols with malonates via a palladium catalyzed Tsuji-Trost type reaction was developed. The reaction was carried out in an organic carbonate solvent which would activate alcohols in situ, replacing the traditional pre-synthesized carbonates. The new process demonstrated high efficiency, high selectivity and high generality. A wide variety of mono-substituted and bis-substituted malonates were selectively produced under different conditions, and this method represents a more step- and atom-economical and environmentally benign synthetic protocol.
The facile and direct formylation of organoboron aromatic compounds with benzodithiolylium tetrafluoroborate
Petruzziello, Diego,Gualandi, Andrea,Jaffar, Hamza,Lopez-Carrillo, Veronica,Cozzi, Pier Giorgio
, p. 4909 - 4917 (2013/08/23)
Organoboron compounds can be used to effect a direct formylation in the absence of transition metals. We report that the direct reaction between boronic derivatives and benzodithiolylium tetrafluoroborate, a commercially available carbenium ionic compound, is possible and provides access to many interesting compounds without the use of transition metals. The direct reaction of the carbenium ion with boronic derivatives results in the formation of substituted arylcarbenium ions, a number of which can be further utilized in materials chemistry or for the direct transformation into other compounds. In addition to the rich chameleonic chemical nature of the benzodithiol intermediate, such species can also undergo a metallation reaction and subsequent treatment with a wide range of electrophiles to access a variety of functional groups (aldehyde, ketone, acid, and alkyl groups). Copyright
ENZYME CATALYSED HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIESTERS, CHAIN LENGTH DEPENDENT REVERSAL OF ENANTIOSELECTIVITY
Bjoerkling, Fredrik,Boutelje, John,Gatenbeck, Sten,Hult, Karl,Norin, Torbjoern,Szmulik, Peter
, p. 1347 - 1352 (2007/10/02)
Enzyme catalysed hydrolyses of dialkylated propanedioic acid diesters have been studied.A novel change of enantioselectivity from pro-S to pro-R in the hydrolysis of ester groups was observed, depending on the chain length of the alkyl substituents of the
