Borylation–reduction–borylation for the formation of 1,4-azaborines
Abstract
Given the current interest in materials containing 1,4-azaborine units, the development of new routes to these structures is important. Carbonyl directed electrophilic borylation using BBr3 is a facile method for the ortho-borylation of N,N-diaryl-amide derivatives. Subsequent addition of Et3SiH results in carbonyl reduction and then formation of 1,4-azaborines that can be protected in situ using a Grignard reagent. Overall, borylation–reduction–borylation is a one-pot methodology to access 1,4-azaborines from simple precursors.
Citation
Kothavale , S S , Iqbal , S A , Hanover , E L , Gupta , A K , Zysman-Colman , E & Ingleson , M J 2023 , ' Borylation–reduction–borylation for the formation of 1,4-azaborines ' , Organic Letters , vol. 25 , no. 49 , pp. 8912-8916 . https://doi.org/10.1021/acs.orglett.3c03731
Publication
Organic Letters
Status
Peer reviewed
ISSN
1523-7060Type
Journal article
Description
This project has received funding from the Leverhulme Trust (grant Number RPG-2022-032) and the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (Grant Agreement No. 769599). M.J.I. and E.Z.-C. also thank the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517/1) for support.Collections
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