Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides
Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides
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DOI：
10.1021/jo991342u
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发表时间：
2000-01-14
影响因子：
3.6
通讯作者：
Hildebrand, JP
中科院分区：
文献类型：
--
作者：
Bolm, C;Hildebrand, JP
采用钯催化交叉偶联的直接方法，高收率地合成了多种n -芳基化亚胺。可变取代模式的芳基溴化物被发现是最有效的偶联伙伴，而芳基碘化物则表现出不可预测的行为，需要锂或银盐作为添加剂来确保在可接受的产率下形成产物。(S)-2-（2'-溴苯基）-4-叔丁基恶唑啉与对映体纯(-)-(RS)-S-甲基-S-苯基亚砜亚胺偶联得到相应的单一非对映体产物，表明钯催化的芳基化反应以立体定向的方式进行。与二溴苯的反应在所有情况下都产生了单磺胺酰芳烃，这表明，磺胺酰部分的引入使芳烃失活，从而阻止了第二次偶联步骤。
Various N-arylated sulfoximines have been synthesized in high yield by a direct approach which is based on a palladium-catalyzed cross-coupling strategy. Aryl bromides of variable substitution pattern were found to be the most effective coupling partners, whereas aryl iodides showed a nonpredictable behavior requiring lithium or silver salts as additives to ensure product formation in acceptable yields. Coupling of (S)-2-(2'-bromophenyl)-4-tert-butyloxazoline with enantiomerically pure (-)-(RS)-S-methyl-S-phenylsulfoximine afforded the corresponding product in good yield as a single diastereomer, showing that the palladium-catalyzed arylation proceeds in a stereospecific manner. The reaction with dibromobenzenes yielded the monosulfonimidoyl arenes in all cases, suggesting that, the introduction of the sulfonimidoyl moiety deactivates the arene, thus preventing a second coupling step.