Borylation–reduction–borylation for the formation of 1,4-azaborines

Shantaram S. Kothavale, Saqib A. Iqbal, Emily L. Hanover, Abhishek K. Gupta, Eli Zysman-Colman*, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
2 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)8912-8916
Number of pages5
JournalOrganic Letters
Volume25
Issue number49
Early online date6 Dec 2023
DOIs
Publication statusPublished - 15 Dec 2023

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