Novel Rh catalysis in cross-coupling between alkyl halides and arylzinc compounds possessing ortho-COX (X = OR, NMe2, or Ph) groups.
Novel Rh catalysis in cross-coupling between alkyl halides and arylzinc compounds possessing ortho-COX (X = OR, NMe2, or Ph) groups.
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DOI：
10.1021/ol060969d
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发表时间：
2006-07
期刊：
影响因子：
5.2
通讯作者：
Hideki Takahashi;S. Inagaki;Y. Nishihara;T. Shibata;K. Takagi
中科院分区：
文献类型：
--
作者：
Hideki Takahashi;S. Inagaki;Y. Nishihara;T. Shibata;K. Takagi
Rh-dppf被发现是一种有效的催化剂，可促进含-氢的伯烷基卤化物与邻位上含有酯、酰胺或酮等羰基的芳基锌化合物之间的交叉偶联。在催化条件下，卤化物上的各种官能团如酯、腈或酰基酸基团均可耐受。没有邻羰基的芳基锌化合物与3-碘丙酸乙酯反应良好，表明羰基与Rh之间的分子内相互作用促进了还原消除。
[reaction: see text] Rh-dppf was found to be an efficient catalyst for the cross-coupling between primary alkyl halides bearing beta-hydrogens and arylzinc compounds possessing carbonyl groups such as ester, amide, or ketone at the ortho position. Various functional groups such as ester, nitrile, or acyloxylate moieties on the halides were tolerated under the catalysis conditions. Arylzinc compounds free of ortho-carbonyl groups reacted well with ethyl 3-iodopropanoate, suggesting that the essential intramolecular interaction between carbonyl groups and Rh promotes the reductive elimination.