噻唑
恶唑
化学
位阻效应
脱质子化
钯
羧酸盐
组合化学
卤化物
立体化学
脱羧
药物化学
催化作用
光化学
有机化学
离子
作者
Laure Théveau,Cécile Verrier,Pierrik Lassalas,Thibaut Martin,Georges Dupas,Olivier Querolle,Luc Van Hijfte,Francis Marsais,Christophe Hoarau
标识
DOI:10.1002/chem.201101615
摘要
Abstract Both base‐assisted non‐concerted metallation–deprotonation (nCMD) and concerted metallation–deprotonation (CMD) have been identified as two potent operating mechanisms in palladium‐catalysed direct CH coupling of oxazole and thiazole‐4‐carboxylate esters with halides through base‐ and solvent‐effect experiments. Novel C2‐ and C5‐selective CMD direct arylation procedures in oxazole‐ and thiazole‐4‐carboxylate series were then designed by controlling the balance between electronic and steric factors. Notably, charge interactions between the palladium catalyst and substrate were identified as a parameter for controlling selectivity and reducing the impact of steric factors in the CMD reaction.
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