Patents by Inventor Paul Knochel
Paul Knochel 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: 11236113Abstract: The invention relates to hydrocarbon-soluble halogen or thiolate/magnesium exchange reagents of the general formula R1MgR11-n(OR3)n.LiOR2.(1?n)LiOR3.aDonor in which: R1 is a C1-C8 alkyl and OR2 as well as OR3 are same or different and represent primary, secondary, or tertiary alkoxide residues having 3 to 18 carbon atoms, wherein R2 and/or R3 can for their part contain an alkoxy substituent OR4; a assumes a value of 0 to 2, n assumes a value between 0 and 1, and the donor is an organic molecule containing at least 2 nitrogen atoms.Type: GrantFiled: September 20, 2018Date of Patent: February 1, 2022Assignee: Albemarle Germany GmbHInventors: Paul Knochel, Dorothée Ziegler, Meike Simon
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Publication number: 20200239496Abstract: The invention relates to hydrocarbon-soluble halogen or thiolate/magnesium exchange reagents of the general formula R1MgR11?n(OR3)n·LiOR2·(1?n)LiOR3·aDonor in which: R1 is a C1-C8 alkyl and OR2 as well as OR3 are same or different and represent primary, secondary, or tertiary alkoxide residues having 3 to 18 carbon atoms, wherein R2 and/or R3 can for their part contain an alkoxy substituent OR4; a assumes a value of 0 to 2, n assumes a value between 0 and 1, and the donor is an organic molecule containing at least 2 nitrogen atoms.Type: ApplicationFiled: September 20, 2018Publication date: July 30, 2020Inventors: Paul Knochel, Dorothée Ziegler, Meike Simon
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Patent number: 10087126Abstract: The invention relates to a process for the preparation of compound of formula (I) wherein R1 is halogen and R2 is halogen or hydrogen; comprising a) reacting the compound of formula (II) in an aprotic organic solvent in the presence of an aprotic polar co-solvent with a magnesium amide base followed by a halogenating agent, to the compound of formula I wherein R1 is halogen and R2 is hydrogen, and b) reacting the compound of formula (I), wherein R1 is chloro and R2 is hydrogen, in an aprotic organic solvent in the presence of an aprotic polar co-solvent with a magnesium amide base followed by a halogenating agent to a compound of formula I, wherein R1 is chloro and R2 is halogen.Type: GrantFiled: October 8, 2015Date of Patent: October 2, 2018Assignee: SYNGENTA PARTICIPATIONS AGInventors: Helmars Smits, Paul Knochel, Thomas Klatt, Matthias Becker
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Publication number: 20170297981Abstract: The invention relates to a process for the preparation of compound of formula (I) wherein R1 is halogen and R2 is halogen or hydrogen; comprising a) reacting the compound of formula (II) in an aprotic organic solvent in the presence of an aprotic polar co-solvent with a magnesium amide base followed by a halogenating agent, to the compound of formula I wherein R1 is halogen and R2 is hydrogen, and b) reacting the compound of formula (I), wherein R1 is chloro and R2 is hydrogen, in an aprotic organic solvent in the presence of an aprotic polar co-solvent with a magnesium amide base followed by a halogenating agent to a compound of formula I, wherein R1 is chloro and R2 is halogen.Type: ApplicationFiled: October 8, 2015Publication date: October 19, 2017Applicant: Syngenta Participations AGInventors: Helmars SMITS, Paul KNOCHEL, Thomas KLATT, Matthias BECKER
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Patent number: 9688701Abstract: Compounds, methods of making the compounds and methods of using the compounds are generally described herein. The compounds are generally of formula R1R2N—ZnY LiY, wherein R1 and R2 are independently selected from H, aryl, heteroaryl containing one or more heteroatoms, alkyl, alkenyl, alkynyl, and silicon derivatives thereof; and each Y is independently selected from F, Cl, Br, I, CN, SCN, NCO, HalO3, HalO4, NO3, BF4, PF6, H, an alcoholate of formula OR5, a carboxylate of formula R5CO2; a thiolate of formula SR5, R5P(O)O2, SCOR5, SCSR5, OnSR5 and NOn, wherein n=2 or 3; wherein R5 is selected from substituted or unsubstituted aryls or heteroaryls containing 3 to 24 carbon atoms and one or more heteroatoms selected from B, O, N, S, Se, P, linear, branched or cyclic, substituted or unsubstituted alkyls, alkenyls, alkynyls or H; and wherein Hal is a halogen selected from Cl, Br and I.Type: GrantFiled: April 1, 2016Date of Patent: June 27, 2017Assignee: Ludwig-Maximilians-Universitat MunchenInventors: Paul Knochel, Marc Mosrin
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Publication number: 20160215000Abstract: Compounds, methods of making the compounds and methods of using the compounds are generally described herein. The compounds are generally of formula R1R2N—ZnY LiY, wherein R1 and R2 are independently selected from H, aryl, heteroaryl containing one or more heteroatoms, alkyl, alkenyl, alkynyl, and silicon derivatives thereof; and each Y is independently selected from F, Cl, Br, I, CN, SCN, NCO, HalO3, HalO4, NO3, BF4, PF6, H, an alcoholate of formula OR5, a carboxylate of formula R5CO2; a thiolate of formula SR5, R5P(O)O2, SCOR5, SCSR5, OnSR5 and NOn, wherein n=2 or 3; wherein R5 is selected from substituted or unsubstituted aryls or heteroaryls containing 3 to 24 carbon atoms and one or more heteroatoms selected from B, O, N, S, Se, P, linear, branched or cyclic, substituted or unsubstituted alkyls, alkenyls, alkynyls or H; and wherein Hal is a halogen selected from Cl, Br and I.Type: ApplicationFiled: April 1, 2016Publication date: July 28, 2016Inventors: Paul Knochel, Marc Mosrin
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Patent number: 9334237Abstract: A reagent of the formula R1R2N—ZnY LiY??(I) wherein R1 and R2 are independently, selected from H, aryl or heteroaryl, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, or silyl derivatives thereof; and R1 and R2 together form part of a cyclic or polymeric structure; R1 and/or R2 is not H; Y is F, Cl, Br, I, CN, SCN, NCO or HalOn, wherein n=3 or 4 and Hal is Cl, Br or I; NO3; BF4; PF6; H; a carboxylate of formula R5CO2; an alcoholate of formula OR5; a thiolate of formula SR5; R5P(O)O2; or SCOR5; or SCSR5; OnSR5; wherein n=2 or 3; or NOn, wherein n=2 or 3; and a derivative thereof; wherein R5 is an aryl or heteroaryl, linear, branched or cyclic, alkyl, alkenyl, alkynyl, or derivatives thereof, or H; or as adduct with a solvent; and preparation and use thereof.Type: GrantFiled: February 11, 2010Date of Patent: May 10, 2016Assignee: Ludwig-Maximilians-Universitat MunchenInventors: Paul Knochel, Marc Mosrin
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Patent number: 9273070Abstract: Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions.Type: GrantFiled: December 21, 2011Date of Patent: March 1, 2016Inventors: Paul Knochel, Sebastian Bernhardt, Georg Manolikakes
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Publication number: 20140031545Abstract: Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions.Type: ApplicationFiled: December 21, 2011Publication date: January 30, 2014Applicant: LUDWIG-MAXIMILIAN-UNIVERSITAT MUNCHENInventors: Paul Knochel, Sebastian Bernhardt, Georg Manolikakes
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Patent number: 8513416Abstract: The present invention relates to zinc amide bases of the general formula (I) (R1R2N)2—Zn.aMgX12.bLiX2??(I) wherein R1 and R2 are each independently selected from substituted or unsubstituted, linear or branched alkyl, alkenyl, alkynyl or silyl derivatives thereof, and substituted or unsubstituted aryl or heteroaryl, and wherein R1 and R2 can form together a ring structure, or R1 and/or R2 can be part of a polymer structure; X12 is a divalent anion or two monovalent anions that are independent from each other; X2 is a monovalent anion; a is >0; and b is >0. The zinc amide bases can be used, amongst other things, for deprotonation and metallization of aromatics.Type: GrantFiled: May 14, 2008Date of Patent: August 20, 2013Assignee: Ludwig-Maximilians-Universitat MuenchenInventors: Paul Knochel, Stefan Wunderlich
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Patent number: 8470982Abstract: The present invention relates to anhydrous solutions of MX3-Z LiA in a solvent, wherein M is a lanthanide including lanthanum, or yttrium or indium; z>0; and X and A are independently or both monovalent anions, preferably Cl, Br or I. The solution is readily prepared by dissolving or suspending MX3 or its hydrate and z equiv LiA in water or hydrophilic solvents, or mixtures thereof, removing the solvent under vacuum and dissolving the resulting powder in another solvent. The solution of MX3-Z LiA can advantageously be used e.g. in addition reactions of Grignard reagents to ketones and imines. Even the catalytic use of MX3-Z LiA is possible.Type: GrantFiled: September 1, 2006Date of Patent: June 25, 2013Assignee: Ludwig-Maximilians-UniversitaetInventors: Paul Knochel, Arkady Krasovskiy, Felix Kopp
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Patent number: 8134005Abstract: The present application relates to mixed Mg/Li amides of the general formula R1R2N—Mg(NR3R4)mX,.Type: GrantFiled: January 18, 2007Date of Patent: March 13, 2012Assignee: Ludwig-Maximilians-Universitat MünchenInventors: Paul Knochel, Arkady Krasovskiy, Valeria Krasovskaya, Christoph Josef Rohbogner, Giuliano Cesar Clososki
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Publication number: 20110288296Abstract: The application relates to a reagent of the general formula R1R2N—ZnY LiY??(I) wherein R1, R2 are, independently, selected from H, substituted or unsubstituted aryl or heteroaryl containing one or more heteroatoms, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, or silyl derivatives thereof; and R1 and R2 together can be part of a cyclic or polymeric structure; and wherein at least one of R1 and R2 is other than H; Y is selected from the group consisting of F; Cl; Br; I; CN; SCN; NCO; Halon, wherein n=3 or 4 and Hal is selected from Cl, Br and I; NO3; BF4; PF6; H; a carboxylate of the general formula RXCO2; an alcoholate of the general formula ORX; a thiolate of the general formula SRX; RXP(O)O2; or SCORX; or SCSRX; OnSRx; wherein n=2 or 3; or NOn, wherein n=2 or 3; and a derivative thereof; wherein Rx is a substituted or unsubstituted aryl or heteroaryl containing one or more heteroatoms, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, orType: ApplicationFiled: February 11, 2010Publication date: November 24, 2011Inventors: Paul Knochel, Marc Mosrin
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Publication number: 20110084230Abstract: The present application discloses a process for preparing a compound of the general formula R1-M1-Ad.zLiX (I) by reacting a compound R1-A (III) with an element M1 in the presence of lithium salts. The application also discloses a process for preparing a compound of the general formula R1m-M3-Tm.zLiX (II) by reacting a compound R1-A (III) with an M3-containing compound in the presence of lithium salts and in the presence of an elemental metal M2. The metal M3 may be selected from Al, Mn, Cu, Zn, Sn, Ti, In, La, Ce, Nd, Y, Li, Sm, Bi, Mg, B, Si and S.Type: ApplicationFiled: April 3, 2007Publication date: April 14, 2011Inventors: Paul Knochel, Andrei Gavryushin, Vladimir Malakhov, Arkady Krasovskiy
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Publication number: 20100184977Abstract: Organozinc compounds of the type R1—Ar1—ZnY (1) can be reacted with different functionalized aryl halides R2—Ar2—X (2) in the presence of catalytic amounts of Ni or Fe in a polar solvent or solvent mixture to form polyfunctional biaryles of the type R1—Ar1—Ar2—R2 (3). Organozinc compounds of the type (1) can be represented by the transmetallation reaction of functionalized aryl magnesium halides or lithium aryl compounds with e.g. ZnBr2.Type: ApplicationFiled: September 12, 2006Publication date: July 22, 2010Inventors: Paul knochel, Andrei Gavriushin, Christiane Charlotte Kofink, Georg Manolikakes
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Publication number: 20100160632Abstract: The present invention relates to zinc amide bases of the general formula (I) (R1R2N)2—Zn.aMgX12.bLiX2??(I) wherein R1 and R2 are each independently selected from substituted or unsubstituted, linear or branched alkyl, alkenyl, alkynyl or silyl derivatives thereof, and substituted or unsubstituted aryl or heteroaryl, and wherein R1 and R2 can form together a ring structure, or R1 and/or R2 can be part of a polymer structure; X12 is a divalent anion or two monovalent anions that are independent from each other; X2 is a monovalent anion; a is >0; and b is >0. The zinc amide bases can be used, amongst other things, for deprotonation and metallization of aromatics.Type: ApplicationFiled: May 14, 2008Publication date: June 24, 2010Inventors: Paul Knochel, Stefan Wunderlich
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Publication number: 20100144516Abstract: The present application relates to mixed Mg/Li amides of the general formula R1R2N—Mg—NR3R4.Type: ApplicationFiled: January 4, 2008Publication date: June 10, 2010Inventors: Giuliano Cesar Clososki, Christoph Josef Rohbogner, Paul Knochel
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Publication number: 20090326235Abstract: The present invention relates to anhydrous solutions of MX3-Z LiA in a solvent, wherein M is a lanthanide including lanthanum, or yttrium or indium; z>0; and X and A are independently or both monovalent anions, preferably Cl, Br or I. The solution is readily prepared by dissolving or suspending MX3 or its hydrate and z equiv LiA in water or hydrophilic solvents, or mixtures thereof, removing the solvent under vacuum and dissolving the resulting powder in another solvent. The solution of MX3-Z LiA can advantageously be used e.g. in addition reactions of Grignard reagents to ketones and imines. Even the catalytic use of MX3-Z LiA is possible.Type: ApplicationFiled: September 1, 2006Publication date: December 31, 2009Inventors: Paul Knochel, Arkady Krasovskiy, Felix Kopp
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Publication number: 20090176988Abstract: The present application relates to mixed Mg/Li amides of the general formula R1R2N—Mg(NR3R4)mX,m zLiY (II) wherein R1, R2, R3, and R4 are, independently, selected from H, substituted or unsubstituted aryl or heteroaryl containing one or more heteroatoms, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, or silyl derivatives thereof; and R1 and R2 together, or R3 and R4 together can be part of a cyclic or polymeric structure; and wherein at least one of R1 and R2 and at least one of R3 and R is other than H; X and Y are, independently, selected from the group consisting of F; Cl; Br; I; CN; SCN; NCO; HalOn, wherein n=3 or 4 and Hal is selected from Cl, Br and I; NO3; BF4; PF6; H; a carboxylate of the general formula RXCO2; an alcoholate of the general formula ORX; a thiolate of the general formula SRX; RXP(O)O2; or SCORX; or SCSRX; OnSRx, wherein n=2 or 3; or NOn, wherein n=2 or 3; and a derivative thereof; wherein Rx is a substituted or unsubstituted aryl or heteroaryl containiType: ApplicationFiled: January 18, 2007Publication date: July 9, 2009Inventors: Paul Knochel, Arkady Krasovskiy, Valeria Krasovskaya, Christoph Josef Rohbogner, Giuliano Cesar Clososki
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Publication number: 20080269514Abstract: The present invention relates to a process for the formation of carbon-carbon bonds starting from a copper compound of an aryl, heteroaryl, alkene or alkine and an aryl, heteroaryl, alkene or alkine compound having a suitable leaving group. The copper compounds can be prepared inter alia by means of transmetalliziation from a Grignard or lithium compound. Cross-coupling of these compounds with e.g. a halogen-substituted aryl compound is carried out by means of an iron or cobalt catalyst using suitable solvents and suitable additives.Type: ApplicationFiled: October 11, 2005Publication date: October 30, 2008Applicant: SALTIGO GMBHInventors: Paul Knochel, Ioannis Sapountzis, Tobias Korn, Wenwei Lin, Christiane Charlotte Kofink