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首页> 外文期刊>Chemistry: A European journal >Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates
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Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates

机译：碱辅助，钯催化的卤代甲烷直接C-H偶联中区域控制的机理选择：恶唑-和噻唑-4-羧酸酯的第一种方法

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摘要

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 C-H 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.
机译：碱辅助的非一致性金属化-去质子化（nCMD）和协同金属化-去质子化（CMD）已被确定为钯催化的恶唑和噻唑-4-羧酸酯与卤化物通过碱直接通过CH偶联的两个有效操作机理。和溶剂效应实验。然后通过控制电子和空间因素之间的平衡，设计了恶唑-和噻唑-4-羧酸酯系列中新颖的C2-和C5-选择性CMD直接芳基化方法。值得注意的是，钯催化剂和底物之间的电荷相互作用被确定为控制选择性和减少CMD反应中空间因素的影响的参数。

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