99-15-0Relevant articles and documents
Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light
Kyne, Sara Helen,Li, Jiacheng,Siang Tan, Suan,Wai Hong Chan, Philip
supporting information, (2022/01/11)
A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.
Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation
Kim, Yongju,Kim, Jonghoon,Park, Seung Bum
supporting information; experimental part, p. 17 - 20 (2009/08/07)
We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of α,β-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).
A study of amidocarbonylation reactions catalyzed by Pd/HZSM-5
Ke, Wu Yang,Xuan, Zhen Jiang
, p. 806 - 809 (2007/10/03)
A HZSM-5-supported palladium catalyst, which was prepared by the conventional impregnation method, was utilized in amidocarbonylation reactions. Several important parameters were optimized to give moderate to excellent yields. The catalyst recycling of Pd/HZSM-5, for the first time, was achieved for at least four run times without depreciation of catalytic activity. The studies of TEM images revealed that agglomeration of the palladium species of Pd/ HZSM-5 catalyst was avoided after reaction, which was quite different from the case of Pd/C catalyst.