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锆催化烯基氨基硼烷的合成:从烯基硼酸酯的可靠制备到烯基溴化物的直接立体发散性获取。

Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides.

机构信息

Institut des Sciences Moléculaires, UMR 5255, CNRS, Université de Bordeaux, 351 Cours de la libération, 33405 Talence, France.

出版信息

Org Lett. 2020 Apr 3;22(7):2838-2843. doi: 10.1021/acs.orglett.0c00908. Epub 2020 Mar 24.

DOI:10.1021/acs.orglett.0c00908
PMID:32207309
Abstract

A simple procedure has been optimized for the preparation of alkenylaminoborane from alkynes using diisopropylaminoborane and HZrCpCl. Coupled with a magnesium-catalyzed dehydrogenation, it allowed for the use of air- and moisture-stable diisopropylamine. This synthesis has been extended to a one-pot sequence leading directly to bromoalkenes with controlled stereochemistry. As such, it provides an easy, scalable, cheap process to access alkenylboronates and both ()- and ()-bromoalkenes from commercially available alkynes.

摘要

已经优化了一种简单的方法,用于使用二异丙基氨基硼烷和 HZrCpCl 从炔烃制备烯基氨基硼烷。与镁催化脱氢相结合,它允许使用空气稳定和防潮的二异丙胺。该合成已扩展到一锅序列,直接得到具有控制立体化学的溴代烯烃。因此,它提供了一种简单、可扩展、廉价的方法,可从商业上可获得的炔烃获得烯基硼酸酯和 ()-和 ()-溴代烯烃。

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