95929-64-9Relevant articles and documents
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.
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
