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使用高张力环酮亚胺作为亲电试剂,铜催化的丙二烯三组分碳硼化反应

Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles.

作者信息

Deng Hao, Dong Yujie, Shangguan Yu, Yang Fazhou, Han Sheng, Wu Jiaqi, Liang Bo, Guo Hongchao, Zhang Cheng

机构信息

Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, 2 Yuanmingyuan West Road, Beijing 100193, P. R. China.

出版信息

Org Lett. 2021 Jun 4;23(11):4431-4435. doi: 10.1021/acs.orglett.1c01372. Epub 2021 May 13.

Abstract

A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes with bis(pinacolato)diboron and 2-azirines to afford borylated allylaziridines is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2-azirines facilitates the reaction. More chemical transformations of borylated allylaziridines are also reported.

摘要

描述了一种非对映选择性铜和NHC配体催化的丙二烯与双(频哪醇)二硼和2-氮杂环丙烷的三组分双官能化反应,以得到硼化的烯丙基氮杂环丙烷。该反应具有完全的非对映选择性和良好的产率,并且还对相应的硼化产物进行了进一步的氯化反应。据信,2-氮杂环丙烷的高环张力促进了该反应。还报道了硼化烯丙基氮杂环丙烷的更多化学转化。

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