WO2012085170A3 - Process for making organoboron compounds, products obtainable thereby, and their use - Google Patents

Process for making organoboron compounds, products obtainable thereby, and their use Download PDF

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Publication number
WO2012085170A3
WO2012085170A3 PCT/EP2011/073716 EP2011073716W WO2012085170A3 WO 2012085170 A3 WO2012085170 A3 WO 2012085170A3 EP 2011073716 W EP2011073716 W EP 2011073716W WO 2012085170 A3 WO2012085170 A3 WO 2012085170A3
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WO
WIPO (PCT)
Prior art keywords
reactions
organoboron
cat
independently represents
atom
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PCT/EP2011/073716
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French (fr)
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WO2012085170A2 (en
Inventor
Benjamin HAAG
Paul Knochel
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Haag Benjamin
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Publication of WO2012085170A2 publication Critical patent/WO2012085170A2/en
Publication of WO2012085170A3 publication Critical patent/WO2012085170A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/30—Nitrogen atoms non-acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D343/00—Heterocyclic compounds containing rings having sulfur and selenium or sulfur and tellurium atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)

Abstract

A process for making organoboron compounds is disclosed in which at least one organic compound having at least one Cl, Br, or I atom or at least one nucleophilic leaving group substituent is reacted with at least one boron-containing reagent represented by the chemical formula (IA) or (IB): B(YR1)3 (IA) [Cat]n+[B(YR1)4 -]n (IB) in the presence of at least one oxidizable metal or oxidizable metal complex, wherein each Y independently represents an oxygen atom, a sulfur atom, or −NR'-, each R1 and each R' independently represents an organic moiety comprising up to 15 carbon atoms and, optionally, one or more hetero atoms, Cat is a cation or mixture of cations, and n is a positive number in the range from 1 to 3. The organoboron products obtained by this process are useful for conducting coupling reactions and reactions with aldehydes. Due to their selectivity, such reactions may be conducted in protic solvents, such as water and alcohols, and sensitive functional groups in the reactants are maintained in the final product. The organoboron products are stable, so that they maintain their activity during storage.
PCT/EP2011/073716 2010-12-22 2011-12-22 Process for making organoboron compounds, products obtainable thereby, and their use WO2012085170A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201061425815P 2010-12-22 2010-12-22
US61/425,815 2010-12-22

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WO2012085170A2 WO2012085170A2 (en) 2012-06-28
WO2012085170A3 true WO2012085170A3 (en) 2012-10-26

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103554094B (en) * 2013-11-19 2016-04-27 郑州西格玛化工有限公司 One prepares 2, the method for 2 '-dipyridyl-4,4 '-(5-hexyl-2-thiophene)
BR112020022220A2 (en) * 2018-06-01 2021-02-02 Autophagysciences Inc. new compound and pharmaceutical composition comprising the same

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
"Suspensions: Fundamentals and Applications in the Petroleum Industry", vol. 42, 1 January 1964, AMERICAN CHEMICAL SOCIETY, Washington, DC, ISSN: 0065-2393, article DIETMAR SEYFERTH ET AL: "Synthesis of B-Organofunctional Borazine Derivatives", pages: 259 - 265, XP055027652 *
ADONIN NICOLAI YU ET AL: "Polyfluoroorganoboron-oxygen compounds. 7+. Studies of conversion of [(C6HnF5-n)B(OMe)3]- into [(C6HnF5-n)2B(OMe)2]- (n = 0, 1)", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, INSTITUTE OF ORGANIC CHEMISTRY & BIOCHEMISTRY, PRAGUE; CZ, vol. 73, no. 12, 1 January 2008 (2008-01-01), pages 1681 - 1692, XP009161323, ISSN: 0010-0765, DOI: 10.1135/CCCC20081681 *
ADONIN NICOLAY YU ET AL: "Polyfluoroorganoboron-oxygen compounds. 4. Lithium pentafluorophenyltrimethoxyborate, Li[C6F5B(OMe)3], reactions with selected electrophiles and nucleophiles", ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 631, no. 13-14, 1 October 2005 (2005-10-01), pages 2638 - 2646, XP009161320, ISSN: 0044-2313, [retrieved on 20051019] *
ANULEWICZ-OSTROWSKA ROMANA ET AL: "Synthesis and characterization of bromomagnesium[(bispentafluorophenyl)diethoxyborate]", MAIN GROUP METAL CHEMISTRY, TEL AVIV, IL, vol. 25, no. 8, 1 January 2002 (2002-01-01), pages 501 - 504, XP009161324, ISSN: 0792-1241 *
BENJAMIN A. HAAG ET AL: "Practical One-Pot Preparation of Magnesium Di(hetero)aryl- and Magnesium Dialkenylboronates for Suzuki-Miyaura Cross-Coupling Reactions", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 50, no. 32, 1 August 2011 (2011-08-01), pages 7290 - 7294, XP055033126, ISSN: 1433-7851, DOI: 10.1002/anie.201103022 *
BROWN HERBERT C ET AL: "Organoboranes. 48. Improved procedures for the preparation of boronic and borinic esters", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 5, no. 11, 1 November 1986 (1986-11-01), pages 2300 - 2303, XP009161321, ISSN: 0276-7333 *
JIANG B ET AL: "alpha-(Trifluoromethyl)ethenyl boronic acid as a useful trifluoromethyl containing building block. Preparation and palladium-catalysed coupling with aryl halides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 42, no. 24, 11 June 2001 (2001-06-11), pages 4083 - 4085, XP004240858, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(01)00636-0 *
KLIS TOMASZ ET AL: "Formation of arylboron compounds from arylmagnesium reagents and trialkoxyboranes", MAIN GROUP METAL CHEMISTRY, TEL AVIV, IL, vol. 25, no. 8, 1 January 2002 (2002-01-01), pages 479 - 484, XP009161325, ISSN: 0792-1241, DOI: 10.1515/MGMC.2002.25.8.479 *

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