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

Mélodie Birepinte; Virginie Liautard; Laurent Chabaud; Mathieu Pucheault

doi:10.1021/acs.orglett.0c00908

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

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

Authors

Mélodie Birepinte¹, Virginie Liautard¹, Laurent Chabaud¹, Mathieu Pucheault¹

Affiliation

¹ Institut des Sciences Moléculaires, UMR 5255, CNRS, Université de Bordeaux, 351 Cours de la libération, 33405 Talence, France.

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

Abstract

A simple procedure has been optimized for the preparation of alkenylaminoborane from alkynes using diisopropylaminoborane and HZrCp₂Cl. 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 (E)- and (Z)-bromoalkenes from commercially available alkynes.

Publication types

Research Support, Non-U.S. Gov't