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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.

SUBMITTER: Kothavale SS

PROVIDER: S-EPMC10729022 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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Borylation-Reduction-Borylation for the Formation of 1,4-Azaborines.

Kothavale Shantaram S SS Iqbal Saqib A SA Hanover Emily L EL Gupta Abhishek K AK Zysman-Colman Eli E Ingleson Michael J MJ

Organic letters 20231206 49

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- ...[more]

PMID: 38055858

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