7476-41-7Relevant articles and documents
Synthesis and evaluation of 1,1,7,7-tetramethyl-9-azajulolidine (TMAJ) as a highly active derivative of N,N-dimethylaminopyridine
Tsutsumi, Tomohiro,Saitoh, Arisa,Kasai, Tomoyo,Chu, MengYue,Karanjit, Sangita,Nakayama, Atsushi,Namba, Kosuke
supporting information, (2020/05/28)
1,1,7,7-Tetramethyl-9-azajulolidine (TMAJ), which theoretical studies have suggested as a highly active DMAP analog, was synthesized for the first time. The catalytic activity of TMAJ was confirmed by the acetylation reactions of various tert-alcohols. TMAJ showed much higher catalytic activity than DMAP and one of the highest activity levels among the conventional DMAP analogs. These experimental results were in good agreement with the previous theoretical studies.
N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes
Ishii, Takuya,Ota, Kenji,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 14073 - 14077 (2019/10/11)
The N-heterocyclic carbene-catalyzed radical relay enables the vicinal alkylacylation of styrenes, acrylates and acrylonitrile using aldehydes and tertiary alkyl carboxylic acid-derived redox-active esters. This protocol introduces tertiary alkyl groups and acyl groups to C-C double bonds with complete regioselectivity to produce functionalized ketone derivatives. The radical relay mechanism involves single electron transfer from the enolate form of a Breslow intermediate and radical addition of the resultant alkyl radical to the alkene followed by radical-radical coupling.
Visible Light Mediated Reductive Cleavage of C-O Bonds Accessing α-Substituted Aryl Ketones
Speckmeier, Elisabeth,Padié, Clément,Zeitler, Kirsten
supporting information, p. 4818 - 4821 (2015/10/12)
C-O σ-bonds in multifaceted benzoin derivatives can be effectively cleaved as acetates using catalytic amounts of [Ru(bpy)3]Cl2 as photoredox catalyst in combination with Hantzsch ester and triethylamine as a sacrificial electron donor. This mild and operationally simple method is applicable to a great variety of substrates. Homo- and cross-benzoins, which are easily accessed by NHC (N-heterocyclic carbene) catalysis, with both electron-withdrawing and electron-donating substituents, including aryl halogenides, can be employed. The deoxygenated counterparts are isolated in good to excellent yields. These broadly accessible, α-substituted (nonsymmetric) aryl ketones are versatilely applicable for further transformations as illustrated by the syntheses of 2-arylbenzofurans.