A general and convenient selective direct arylation of the 3-position of triimidazo[1,2-a:1’,2’-c:1’’,2’’-e][1,3,5]triazine (1) with (hetero)aryl halides in DMA was successfully achieved in the presence of K2CO3 as the base and a catalyst precursor consisting of Pd(OAc)2 and P(2-furyl)3. Electron-poor and -rich (hetero)aryl moieties, including the strongly deactivated and sterically encumbered 2,4,6-trimethoxyphenyl unit, are well tolerated in the electrophilic partner. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium-(II) halide species onto the triazine ring.
Synthesis of 3-Aryl Substituted Triimidazotriazines via Regioselective Direct Arylation
Ballerini L.Secondo
Methodology
;Del Vecchio A.Penultimo
Methodology
;Bellina F.
Conceptualization
2024-01-01
Abstract
A general and convenient selective direct arylation of the 3-position of triimidazo[1,2-a:1’,2’-c:1’’,2’’-e][1,3,5]triazine (1) with (hetero)aryl halides in DMA was successfully achieved in the presence of K2CO3 as the base and a catalyst precursor consisting of Pd(OAc)2 and P(2-furyl)3. Electron-poor and -rich (hetero)aryl moieties, including the strongly deactivated and sterically encumbered 2,4,6-trimethoxyphenyl unit, are well tolerated in the electrophilic partner. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium-(II) halide species onto the triazine ring.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
