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Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles
Synlett ( IF 2 ) Pub Date : 2020-01-02 , DOI: 10.1055/s-0039-1690779
Hong-Gang Cheng 1 , Qianghui Zhou 1, 2 , Chenggui Wu 1
Affiliation  

Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Salient features of this research include readily available substrates, use of the potassium salt of 5-norbornene-2-carboxylic acid as a catalytic mediator as well as a base, and excellent regioselectivity for the cleavage of epoxides. This mild, chemoselective, scalable, atom- and step-economic protocol offers a straightforward approach for the assembly of isochroman and 2,3-dihydrobenzofuran scaffolds.

中文翻译:

环氧化物在 Catellani 反应中作为双官能化烷基化试剂用于杂环组装

报道了一种协同催化系统,由 Pd 与二环己基(2',4',6'-三异丙基联苯-2-基)膦(XPhos)和 5-降冰片烯-2-羧酸的钾盐组成的络合物,允许在用于组装杂环的 Catellani 型反应中使用环氧化物作为双官能化烷基化试剂。这项研究的显着特点包括容易获得的底物、使用 5-降冰片烯-2-羧酸的钾盐作为催化介质和碱,以及出色的环氧化物裂解区域选择性。这种温和、化学选择性、可扩展、原子和步骤经济的协议为异色满和 2,3-二氢苯并呋喃支架的组装提供了一种直接的方法。
更新日期:2020-01-02
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