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Summary

A Spanish public research organization and a University of Spain have developed a procedure to obtain new organoboranes. These chemical compounds are extremely useful as synthetic intermediates in Fine Chemistry (production of drugs, agrochemicals, perfumes, new materials, etc.). Partners interested in a patent license agreement are sought.

Full description

A Spanish public research organisation and a university of Spain have developed a double borylation catalytic procedure of benzaldehyde derivatives to obtain ortho, ortho’ diborylated organoboranes. These compounds are new (not described similar organoboranes, organolithiums or Grignards) and highly valuable as synthetic intermediates for the industrial production of fine chemicals (drugs, agrochemicals, perfumes and new materials).

The chemicals considered as classic organometallics, such as organolithiums or Grignard reagents, are widely used in the Chemical Industry. In recent years, the organoboranes have become a good alternative: they are less harmful, stable in air and water, don’t need to be used at low temperatures and are applicable to a wider variety of molecules.
Organoboranes are extremely versatile synthetic intermediates, because they can be converted into a wide variety of functional groups (alcohols, amines, aldehydes, etc.), and they can be used to create new Carbon-Carbon bonds (coupling reactions).
One of the challenges of the Chemical Industry is to have efficient methods to prepare organoboranes.
A Spanish public organization and a university of Spain have developed a new method to synthesize organoboranes, obtaining hydrazone and oxime aromatic compounds which present two boryl groups in the molecule. This procedure uses as starting material aromatic hydrazones or oximes (benzaldehyde derivatives) which react with a commercial borylating agent in the presence of an Iridium catalyst. The two boryl groups are selectively introduced in the ortho, ortho’ positions to hydrazone or oxime group of the aromatic ring. Another important aspect of this technology is that the reaction proceeds independently to the substituents in the ring (electron donors or acceptors, bulky groups, etc.), so this is a very general and versatile procedure to obtain a wide variety of organoboranes. Depending on the borylating agent employed, boronic acids or esters can be obtained.
These diborylated compounds have a high synthetic value because they can achieve sequential functionalizations in both ortho positions (C2 and C6) with two similar or different electrophyles (including the formation of C-C bonds), so different substituents can be added. They are a new sort of reagent in synthetic organic chemistry, because there are no precedents of similar organoboranes, organolithiums or Grignards compounds.

Innovative Aspects

- These aromatic diborylated compounds are completely new because similar classic organometallic compounds (organolithiums, Grignards, etc.) haven’t been described.
- Organoboranes are synthetic equivalents to classic organometallics but stable in water and air, compatible with a wider variety of functional groups, and less harmful. At industrial scale, it results in significant economic and environmental benefits.
- The synthetic procedure is simple (only one step) and easily scalable.
- This synthetic methodology enables the direct double borylation of Carbon-Hydrogen bonds, instead of needing halogenated compounds as starting material (like the majority of the synthetic procedures used to obtain organoboranes).
- The synthetic procedure is highly general, because it doesn’t depend on the aromatic ring substituents of the starting material. The two boryl groups are exclusively introduced in ortho, ortho’ positions.

Partner expertise sought:

- Type of partner sought: Industrial Partners
- Specific area of activity of the partner: Fine Chemistry
- Task to be performed by the partner sought: patent license agreement: production of drugs, agrochemicals, perfumes or new materials with these new compounds