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A general method for interconversion of boronic acid protecting groups: trifluoroborates as common intermediates
Quentin I Churches1,2, Joel F Hooper1, Craig A Hutton1
1†School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.
The Journal of Organic Chemistry
|May 21, 2015
Summary
A new protocol converts protected boronic acids using organotrifluoroborates. This method overcomes previous limitations, enabling the synthesis of diverse protected boronic acid compounds.
Area of Science:
- Organic Chemistry
- Organoboron Chemistry
Background:
- Protected boronic acids are valuable synthetic intermediates.
- Previous methods faced limitations in converting certain protected boronic acids, like N-Methyliminodiacetyl boronates.
Purpose of the Study:
- To develop a general protocol for interconverting diverse protected boronic acids.
- To enable the synthesis of protected boronic acids resistant to direct conversion.
Main Methods:
- Utilized intermediate organotrifluoroborates for boronic acid interconversion.
- Applied fluorolysis of N-Methyliminodiacetyl boronates at elevated temperatures.
- Employed solvolysis of organotrifluoroborates with trimethylsilyl chloride and bis-nucleophiles.
Main Results:
- Established a general protocol for protected boronic acid interconversion.
- Successfully converted N-Methyliminodiacetyl boronates to trifluoroborates.
- Generated a variety of protected boronic acids through solvolysis.
Conclusions:
- The developed protocol offers a versatile route to diverse protected boronic acids.
- Overcame challenges in synthesizing specific protected boronic acid derivatives.
- Provides a valuable tool for organic synthesis and medicinal chemistry.
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