5005-35-6Relevant articles and documents
Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester: Via chemoselective C(acyl)-O bond activation
Ma, Hongpeng,Bai, Chaolumen,Bao, Yong-Sheng
, p. 17266 - 17272 (2019/06/24)
A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation via C(acyl)-O bond activation of esters by successful suppression of the undesired decarbonylation phenomenon. The catalyst can be reused and shows high activity after eight cycles. The XPS analysis of the catalyst before and after the reaction suggested that the reaction might be performed via a Pd0/PdII catalytic cycle that began with Pd0.
Access to N-Substituted 2-Pyridones by Catalytic Intermolecular Dearomatization and 1,4-Acyl Transfer
Xu, Guangyang,Chen, Ping,Liu, Pei,Tang, Shengbiao,Zhang, Xinhao,Sun, Jiangtao
supporting information, p. 1980 - 1984 (2019/01/04)
A novel rhodium-catalyzed dearomatization of O-substituted pyridines to access N-substituted 2-pyridones has been developed. A computational study suggests a mechanism involving the formation of a pyridinium ylide followed by an unprecedented 1,4-acyl migratory rearrangement from O to C. Furthermore, the chiral dirhodium complexes serve as the catalyst for the asymmetric transformation with excellent enantioselective control. DFT calculations indicate the chirality is transferred from axial chirality to the central stereogenic centre. The stronger π–π interaction and CH–π interaction account for the high enantioselectivity.
4-(N,N -dimethylamino)pyridine hydrochloride as a recyclable catalyst for acylation of inert alcohols: Substrate scope and reaction mechanism
Liu, Zhihui,Ma, Qiaoqiao,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 236 - 239 (2014/01/23)
4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP·HCl), a DMAP salt with the simplest structure, was used as a recyclable catalyst for the acylation of inert alcohols and phenols under base-free conditions. The reaction mechanism was investigated in detail for the first time; DMAP·HCl and the acylating reagent directly formed N-acyl-4-(N′,N′-dimethylamino) pyridine chloride, which was attacked by the nucleophilic substrate to form a transient intermediate that released the acylation product and regenerated the DMAP·HCl catalyst.