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铜催化的环丁酮肟酯与活化烯烃的氧化还原中性氰基芳基化反应。

Copper-Catalyzed Redox-Neutral Cyanoalkylarylation of Activated Alkenes with Cyclobutanone Oxime Esters.

机构信息

Department of Chemistry, School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiaotong University , Xi'an 710049, China.

出版信息

J Org Chem. 2018 Jan 19;83(2):1046-1055. doi: 10.1021/acs.joc.7b02714. Epub 2017 Dec 29.

DOI:10.1021/acs.joc.7b02714
PMID:29239182
Abstract

The copper-catalyzed cyclization of activated alkenes with cyclobutanone O-acyl oximes under redox-neutral conditions has been reported. This facile protocol provided an efficient approach to a variety of cyanoalkylated oxindoles and dihydroquinolin-2(1H)-ones with a broad substrate scope and excellent functional group tolerance. In this reaction, sequential C-C bond cleavage, radical addition, and cyclization processes were involved, wherein multiple bonds were constructed in a one-pot reaction. Mechanistic studies suggest that the reaction probably proceeded via a radical pathway.

摘要

报道了在氧化还原中性条件下,铜催化的活性烯烃与环丁酮 O-酰基肟的环化反应。该简便的方案为各种氰基烷基化的吲哚啉酮和二氢喹啉-2(1H)-酮提供了一种有效的方法,具有广泛的底物范围和优异的官能团耐受性。在这个反应中,涉及到顺序的 C-C 键断裂、自由基加成和环化过程,其中在一锅反应中构建了多个键。机理研究表明,反应可能是通过自由基途径进行的。

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