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钯催化的对映体富集的钾 β-三氟硼酸盐酰胺与各种芳基和杂芳基氯化物的 Suzuki-Miyaura 交叉偶联反应。

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

机构信息

Roy and Diana A. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

出版信息

Org Lett. 2010 Oct 1;12(19):4384-7. doi: 10.1021/ol101865e.

DOI:10.1021/ol101865e
PMID:20831191
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2946850/
Abstract

Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.

摘要

外消旋体富集的钾 β-三氟硼酰胺作为空气稳定的固体,以伪麻黄碱作为手性助剂,以大于 95:5 dr 的比例合成。使用这些手性亲核试剂,与各种芳基和杂芳基氯化物进行 Suzuki-Miyaura 交叉偶联反应,产率良好到优秀。此外,在整个 Suzuki-Miyaura 交叉偶联反应中,非对映选择性得到了保持。

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本文引用的文献

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Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.三氟硼酸盐和单配位钯配合物作为催化剂——Suzuki-Miyaura 偶联的完美组合。
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