Patents by Inventor Patrick Fier
Patrick Fier has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 9758453Abstract: A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.Type: GrantFiled: October 21, 2015Date of Patent: September 12, 2017Assignee: The Board of Trustees of the University of IllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Patent number: 9701635Abstract: The present invention provides compositions and methods for the selective C—H fluorination of nitrogen-containing heteroarenes with AgF2, which has previously been considered too reactive for practical, selective C—H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of F2 gas. The present invention provides a mild and general method for the C—H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF2. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.Type: GrantFiled: July 28, 2014Date of Patent: July 11, 2017Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: John Hartwig, Patrick Fier
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Patent number: 9475756Abstract: Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electron rich, and sterically hindered aryl and vinyl iodides with the combination of CuI, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.Type: GrantFiled: March 5, 2013Date of Patent: October 25, 2016Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: John Hartwig, Patrick Fier
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Patent number: 9452959Abstract: The invention provides compositions and methods of using the compositions in fluorinating aryl precursors containing a leaving group replaceable by fluoride ion. The compositions include a metal ion source, a fluoride ion source, and a compound, which is an aryl precursor of the aryl fluoride, and which has a leaving group replaceable by the fluoride. Exemplary methods of the invention make use of such compositions and methods to prepare an aryl fluoride compound. In an exemplary embodiment, the fluoride ion source is a source of 18F.Type: GrantFiled: June 12, 2013Date of Patent: September 27, 2016Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: John Hartwig, Patrick Fier
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Publication number: 20160185723Abstract: The present invention provides compositions and methods for the selective C—H fluorination of nitrogen-containing heteroarenes with AgF2, which has previously been considered too reactive for practical, selective C—H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of F2 gas. The present invention provides a mild and general method for the C—H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF2. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.Type: ApplicationFiled: July 28, 2014Publication date: June 30, 2016Inventors: John HARTWIG, Patrick FIER
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Publication number: 20160185691Abstract: A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.Type: ApplicationFiled: October 21, 2015Publication date: June 30, 2016Applicant: The Board of Trustees of the University of lllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Publication number: 20150336926Abstract: The invention provides compositions and methods of using the compositions in fluorinating aryl precursors containing a leaving group replaceable by a fluorine atom. The compositions include a metal ion source, a electrophilic fluorine source, a base, and a compound, which is an aryl precursor of the aryl fluoride, and which has a leaving group replaceable by the fluorine atom. Exemplary methods of the invention make use of such compositions and methods to prepare an aryl fluoride compound. In an exemplary embodiment, the electrophilic fluorine source is a source of 18F.Type: ApplicationFiled: December 23, 2013Publication date: November 26, 2015Inventors: John HARTWIG, Patrick FIER
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Publication number: 20150336866Abstract: The synthesis of difluoromethyl ethers and sulfides with a simple, non-ozone-depleting reagent is described. The difluoromethylation of phenols with this reagent occurs at room temperature within minutes with exceptional functional group tolerance. The mild conditions makes possible tandem processes for the conversion of aryl boronic acids, aryl halides and arenes to difluoromethyl ethers. Mechanistic studies support a reaction pathway involving nucleophilic attack of the phenolate to difluorocarbene.Type: ApplicationFiled: December 23, 2013Publication date: November 26, 2015Inventors: John HARTWIG, Patrick FIER
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Patent number: 9193648Abstract: A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.Type: GrantFiled: February 19, 2013Date of Patent: November 24, 2015Inventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Publication number: 20150175508Abstract: The invention provides compositions and methods of using the compositions in fluorinating aryl precursors containing a leaving group replaceable by fluoride ion. The compositions include a metal ion source, a fluoride ion source, and a compound, which is an aryl precursor of the aryl fluoride, and which has a leaving group replaceable by the fluoride. Exemplary methods of the invention make use of such compositions and methods to prepare an aryl fluoride compound. In an exemplary embodiment, the fluoride ion source is a source of 18F.Type: ApplicationFiled: June 12, 2013Publication date: June 25, 2015Inventors: John Hartwig, Patrick Fier
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Publication number: 20150045580Abstract: Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electronrich, and sterically hindered aryl and vinyl iodides with the combination of Cul, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.Type: ApplicationFiled: March 5, 2013Publication date: February 12, 2015Inventors: John Hartwig, Patrick Fier
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Publication number: 20130225815Abstract: A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.Type: ApplicationFiled: February 19, 2013Publication date: August 29, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier