Borylated oximes: versatile building blocks for organic synthesis

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Medicinal Chemistry

Background:

• Borylated organic compounds are valuable synthetic intermediates.
• Developing new synthetic routes to functionalized boron-containing molecules is crucial for expanding their applications.
• Controlling the regioselectivity of borylation reactions is a key challenge.

Purpose of the Study:

• To develop a novel synthetic method for alpha-boryl aldoximes.
• To explore the functionalization of alpha-boryl aldoximes for diverse applications.
• To investigate the utility of borylated aldoximes in peptide conjugation.

Main Methods:

• Synthesis of alpha-boryl aldoximes from alpha-boryl aldehydes.
• Selective modification of the oxime functionality.
• Reduction of alpha-boryl aldoximes and subsequent MIDA deprotection.
• Application in peptide conjugation.

Main Results:

• Successful synthesis of alpha-boryl aldoximes without C-to-N boryl migration.
• Access to a variety of borylated compounds, including heterocycles and N-acetoxyamides.
• Generation of beta-boryl hydroxylamines via reduction and deprotection.
• Demonstrated utility of the boryl aldoxime motif in peptide conjugation.

Conclusions:

• The developed method provides efficient access to alpha-boryl aldoximes.
• The boryl aldoxime motif is a versatile building block for synthesizing diverse borylated compounds.
• This work expands the utility of organoboron compounds in chemical synthesis and bioconjugation.