MIDA Boronates – A revolutionary class of protected boronates
Professor Martin Burke of the Department of Chemistry at UIUC has developed a revolutionary class of protected boronates which can significantly expand the applicability of boronic acids in the chemical and pharmaceutical industries. Boronic acids are key components of Suzuki-Miyaura cross-coupling reactions, one of the most widely used chemical reactions to form carbon-carbon bonds. While representing a powerful building block for these coupling reactions, the full spectrum of boronic acids currently cannot be exploited as certain types of these acids are unstable or difficult to synthesize.
Professor Burke has developed a widely applicable method to (i) protect boronic acids using a trivalent ligand to convert the sp2 hybridized boron of the boronic acid to an sp3 center, thereby stabilizing it towards unwanted reactions and decomposition, and (ii) remove the ligand in a controlled fashion under mild aqueous basic conditions, generating the acid for coupling reactions. A particularly useful example of a protecting ligand is N-methyliminodiacetic acid (MIDA) which can be complexed to boronic acids in a straight-forward manner.
The value of Professor Burke’s protected boronates lies in three general areas, functioning as:
(1) Replacements for boronic acids currently used in carbon-carbon coupling reactions in fine chemical, polymer, and pharmaceutical industries.
(2) Platforms to generate previously inaccessible, yet potentially useful boronic acids enabling the use of 2-heterocyclic, vinyl, cyclopropyl and other derivatives in cross-coupling reactions.
(3) Building blocks for iterative cross-coupling reactions in which protected boronates allow “modular” small molecule synthesis in a manner similar to fabrication of biosynthetic systems such as polypeptides, oligonucleotides, and oligosaccharides.
The University of Illinois at Urbana-Champaign is seeking companies interested in licensing the MIDA boronate patent portfolio to supply quantities of greater than one (1) kg of MIDA boronates to customers. The University wishes to enable “IP-included” sales of the MIDA boronates to promote wide adoption of the technology. Licensees will be granted the right to grant label licenses to the portfolio to make clear that the licensee’s customers have a royalty-free license to the patent rights when used with the purchased MIDA boronates.
Technologies available for licensing
· US Issued Patent 8,013,203 titled System for Controlling the Reactivity of Boronic Acids, to be issued 9/6/2011
· US Provisional Patent Application No. 60/951,405, titled System for Controlling the Reactivity of Boronic Acids, filed 7/23/07 (OTM Reference No. TF07094-PRO)
· US Patent Application No. 13/190,223, titled System for Controlling the Reactivity of Boronic Acids, filed 7/25/2011 (OTM Reference No. TF07094-DIV, priority date 7/23/2007)
· PCT Patent Application No. PCT/US07/84156, titled System for Controlling the Reactivity of Boronic Acids, filed 11/08/07 (OTM Reference No. TF07094-PCT)
· CA Patent Application No. 2,694,068, titled System for Controlling the Reactivity of Boronic Acids, filed 1/23/2010 (OTM Reference No. TF07094-CA)
· IN Patent Application No. 8348/DELNP/2009, titled System for Controlling the Reactivity of Boronic Acids, filed 1/23/2010 (OTM Reference No. TF07094-IN)
· EP Patent Application No. 07844994.9, titled System for Controlling the Reactivity of Boronic Acids, filed 1/23/2010 (OTM Reference No. TF07094-EP)
· CN Patent Application No. 200780053824.3, titled System for Controlling the Reactivity of Boronic Acids, filed 1/23/2010 (OTM Reference No. TF07094-CN)
· JP Patent Application No. 2010-518164, titled System for Controlling the Reactivity of Boronic Acids, filed 1/23/2010 (OTM Reference No. TF07094-JP)
· US Divisional Patent Application No. 13/190,223, titled System for Controlling the Reactivity of Boronic Acids, filed 7/25/2011 (OTM Reference No. TF07094-DIV)
· US Provisional Patent Application No. 61/100,441, titled Slow-Release of Unstable Boronic Acids from Air-Stable MIDA Boronates, filed 9/26/08 (OTM Reference No. TF08188-PRO)
· US Provisional Patent Application No. 61/173,012, titled Slow-Release of Organoboronic Acids in Cross-Coupling Reactions, filed 4/27/09 (OTM Reference No. TF08188-PRO2)
· US Patent Application No. 12/567,443, titled Slow-Release of Organoboronic Acids in Cross-Coupling Reactions, filed 9/25/09 (OTM Reference No. TF08188-US)
· US Provisional Patent Application No. 61/305,603, titled Methods for Forming Protected Organoboronic Acids, filed 2/18/2010 (OTM Reference No. TF09184-PRO)
· PCT Patent Application No. PCT/US11/025446, titled Methods for Forming Protected Organoboronic Acids, filed 2/18/2011 (OTM Reference No. TF09184-PCT)
Contact:
Lisa Dhar
Office of Technology Management (OTM)
University of Illinois at Urbana-Champaign
308 Ceramics Building, MC-243
105 South Goodwin Avenue
Urbana, IL 61801-2901
Office: (217) 333-3715
Fax: (217) 265-5530
E-Mail:
31 August 2011 Page 2