US20060151335A1 - Process for performing an isolated Pd(0) catalyzed reaction electrochemically on an electrode array device - Google Patents

Process for performing an isolated Pd(0) catalyzed reaction electrochemically on an electrode array device Download PDF

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US20060151335A1
US20060151335A1 US11/326,717 US32671706A US2006151335A1 US 20060151335 A1 US20060151335 A1 US 20060151335A1 US 32671706 A US32671706 A US 32671706A US 2006151335 A1 US2006151335 A1 US 2006151335A1
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electrodes
isolated
catalyzed reaction
reaction
electrode array
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Jun Tian
Karl Maurer
Kevin Moeller
Eden Tesfu
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Washington University in St Louis WUSTL
Customarray Inc
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Combimatrix Corp
Washington University in St Louis WUSTL
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Publication of US20060151335A1 publication Critical patent/US20060151335A1/en
Priority to US11/777,972 priority patent/US20080039342A1/en
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/02—Electrodes; Manufacture thereof not otherwise provided for characterised by shape or form
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0046—Sequential or parallel reactions, e.g. for the synthesis of polypeptides or polynucleotides; Apparatus and devices for combinatorial chemistry or for making molecular arrays
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/00497—Features relating to the solid phase supports
    • B01J2219/00527—Sheets
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00585—Parallel processes
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00596—Solid-phase processes
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00599—Solution-phase processes
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00653—Making arrays on substantially continuous surfaces the compounds being bound to electrodes embedded in or on the solid supports
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00659—Two-dimensional arrays
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00709—Type of synthesis
    • B01J2219/00713—Electrochemical synthesis
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00718—Type of compounds synthesised
    • B01J2219/0072—Organic compounds
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00718—Type of compounds synthesised
    • B01J2219/00745—Inorganic compounds
    • B01J2219/0075—Metal based compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • each unique set of molecules in a library can be located proximal to a unique electrode or set of electrodes that can in turn be used to monitor their behavior (Dill et al., Analytica Chimica Acta, 444:69, 2001).
  • This is accomplished by coating the electrode-containing devices with a porous polymer and then utilizing the electrodes to both attach monomers to the chips and then generate reagents capable of performing reactions on the monomers.
  • the Heck reaction is a powerful synthetic tool that allows for the efficient generation of new carbon-carbon bonds.
  • the availability of a Heck reaction on an electrode array device would dramatically expand the types of molecules that could be constructed within a volume proximal to an electrode surface.
  • Such a tool would allow for massively parallel electrochemical synthesis in small volumes on an electrode array device and create arrays containing highly diverse libraries of chemical compounds that are different from each other yet synthesized in parallel.
  • Such combinatorial libraries could be synthesized rapidly, in small volumes and highly diverse. Therefore, there is a need in the art to be able to rapidly create diverse chemical libraries on a single solid electrode array device for large scale screening of combinatorial libraries. The present invention was made to address this need in the art.
  • the present invention provides a process for conducting an isolated Pd(0) catalyzed reaction on a plurality of electrodes, comprising:
  • the isolated Pd(0) catalyzed reaction is selected from the group consisting of a Heck reaction, a Suzuki coupling reaction, displacement of an aryl halide with an RS-nucleophile of NH 2 R nucleophile, coupling an aryl bromide to an aluminoacetylene Al (C ⁇ C—R) 4 Na salt, displacement of an aryl halide with an esterenolate, alkyl group Suzuki coupling (aryl boron reagent with alkyl halide), Stille coupling R—X plus R′SnR′′ 3 , alkyne-BF 3 salt coupling to aryl triflate halide, vinyl-BF 3 salt or alkyne-BF 3 salt coupling, reaction of an alcohol with alkyl/allyl carbonate to make alcohol allyl ether, conversion of an alpha aminoacetylene to a ketene, conversion of Ar—X plus acid chloride to acetylinic ketone, and combinations thereof.
  • the transition metal catalyst for an isolated Pd(0) catalyzed reaction is a palladium (Pd) or a platinum (Pt) catalyst system.
  • a Pd catalyst is stabilized with stabilizer selected from the group consisting of a phosphine ligand, a phosphite ligand, an arsenic derivative, a triphenylphosphine ligand, and combinations thereof.
  • the Pd catalyst is stabilized by a triphenylphosphine ligand.
  • the confining agent is an oxidant added to solution sufficient to convert Pd(0) back to Pd(II).
  • the confining agent is an oxidant selected from the group consisting of substituted or unsubstituted allyl alkyl carbonates, allyl acetate, O2, peroxides, quinines, and combinations thereof. More preferably, the confining agent is a substituted or unsubstituted allyl alkyl carbonate wherein the alkyl moiety can be a C 1-6 alkyl group.
  • the biasing step used a voltage no greater than 2.4 V.
  • the biasing step was performed for a time of from about 1 sec to 3 min.
  • FIG. 1 shows a an electrode array surface under a fluorescent scanner device (Axon Instruments) wherein 1-pyrenemethylacrylate was deposited at selected electrode sites using electrodes as cathodes to reduce Pd(II) to Pd(0).
  • the Pd(0) triggered a Heck reaction between the substrate and the aryl iodide on the surface of the selected electrodes (selected to form a square pattern with an electrode in the middle).
  • the bright spots are the selected electrodes with 1-pyrenemethylacrylate as an indicator.
  • FIG. 3 shows the synthetic scheme for the experiment.
  • an aryl iodide is placed on the chips surface using the same methodology employed in earlier studies (Tesfu et al., J. Am. Chem. Soc. 126:6212, 2004).
  • all of the electrodes on the electrode array device were utilized as cathodes in order to reduce vitamin B 12 .
  • the base served to catalyze an esterification reaction between the hydroxyl groups of the polysaccharide polymer coating the electrode array device and the N-hydroxysuccinimide ester of 4-iodobenzoic acid.
  • the effect of this process was to concentrate the aryl iodide substrate near the electrodes on the electrode array device.
  • the second step in the sequence is the Heck reaction.
  • the Heck reaction is performed by submerging the electrode array device in a 2:7:1 DMF/MeCN/H 2 O solution containing Pd(0Ac) 2 , triphenyl-phosphine, triethylamine, allyl methyl carbonate, and tetrabutyl-ammonium bromide electrolyte.
  • Selected electrodes were turned on as cathodes at a voltage of ⁇ 2.4 V (relative to a Pt auxiliary electrode as an anode) in order to generate a box pattern of electrodes on the array with a dot in the center.
  • the electrodes (Pt surface) were cycled for 0.5 sec on and then 0.1 sec off for 3 min.
  • the reagents generated at any given electrode were confined to the area surrounding the electrode by placing a substrate in the solution above the electrode that consumed the reagent. Briefly, this process was described in connection with the generation of acids and bases confined to a volume on electrode array devices (see, for example, Montgomery U.S. Pat. No. 6,093,302, the disclosure of which is incorporated by reference herein). In previous work, a Pd(II) reagent was generated electrochemically and confined to a region surrounding an electrode (Tesfu et al., J. Am. Chem. Soc. 126:6212, 2004).
  • the Pd(II) reagent was generated by utilizing the electrodes on an electrode array device as anodes to oxidize a Pd(0) reagent added to the solution above the electrode array device.
  • the Pd(II) reagent generated was confined to the electrode sites of its generation with the use of ethyl vinyl ether. The feasibility of this process was demonstrated by performing a Wacker oxidation at selected electrodes on the electrode array.
  • the present invention was motivated by the desire to determine if the electrodes be used as cathodes in order to reduce a Pd(II) reagent to a Pd(0) reagent at pre-selected sites on a microarray device having a plurality of electrode sites (each separately addressable).
  • the problem solved by the present invention was to find an efficient confinement strategy for the Pd(0) reagent generated so that it was confined to one electrode and did not catalyze a reaction at a neighboring electrode. This is necessary in order to be able to perform the Heck reaction (a Pd(0) catalyzed reaction) at selected electrode sites while avoiding the reaction at non-selected electrode sites.
  • the electrode array-based environment must be used to make a normally catalytic reaction stoichiometric thereby confining the catalyst to pre-selected sites on the selected electrode of the array.
  • the isolated Pd(0) catalyzed reaction is selected from the group consisting of a Heck reaction, a Suzuki coupling reaction, displacement of an aryl halide with an RS-nucleophile of NH 2 R nucleophile, coupling an aryl bromide to an aluminoacetylene Al (C ⁇ C—R) 4 Na salt, displacement of an aryl halide with an esterenolate, alkyl group Suzuki coupling (aryl boron reagent with alkyl halide), Stille coupling R—X plus R′SnR′′ 3 , alkyne-BF 3 salt coupling to aryl triflate halide, vinyl-BF 3 salt or alkyne-BF 3 salt coupling, reaction of an alcohol with alkyl/allyl carbonate to make alcohol allyl ether, conversion of an alpha aminoacetylene to a ketene, conversion of Ar—X plus acid chloride to acetylinic ketone, and combinations thereof.
  • a Pd catalyst is stabilized with stabilizer selected from the group consisting of a phosphine ligand, a phosphite ligand, an arsenic derivative, a triphenylphosphine ligand, and combinations thereof. Most preferably, the Pd catalyst is stabilized by a triphenylphosphine ligand.
  • the confining agent is an oxidant added to solution sufficient to convert Pd(0) back to Pd(II).
  • the confining agent is an oxidant selected from the group consisting of substituted or unsubstituted allyl alkyl carbonates, allyl acetate, O2, peroxides, quinines, and combinations thereof. More preferably, the confining agent is a substituted or unsubstituted allyl alkyl carbonate wherein the alkyl moiety can be a C 1-6 alkyl group.
  • the biasing step used a voltage no greater than 2.4 V.
  • the biasing step was performed for a time of from about 1 sec to 3 min.
  • substituted in the context of a moiety of the confining agent, means a moiety independently selected from the group consisting of (1) the replacement of a hydrogen on at least one carbon by a monovalent radical, (2) the replacement of two hydrogens on at least one carbon by a divalent radical, (3) the replacement of three hydrogens on at least one terminal carbon (methyl group) by a trivalent radical, (4) the replacement of at least one carbon and the associated hydrogens (e.g., methylene group) by a divalent, trivalent, or tetravalent radical, and (5) combinations thereof. Meeting valence requirements restricts substitution.
  • Substitution occurs on alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic ring, and polycyclic groups, providing substituted alkyl, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, substituted cycloalkynyl, substituted aryl group, substituted heterocyclic ring, and substituted polycyclic groups.
  • the groups that are substituted on an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic ring, and polycyclic groups are independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic ring, polycyclic group, halo, heteroatom group, oxy, oxo, carbonyl, amide, alkoxy, acyl, acyloxy, oxycarbonyl, acyloxycarbonyl, alkoxycarbonyloxy, carboxy, imino, amino, secondary amino, tertiary amino, hydrazi, hydrazino, hydrazono, hydroxyimino, azido, azoxy, alkazoxy, cyano, isocyano, cyanato, is
  • heteroatom groups can be substituted inside an alkyl, alkenyl, or alkylnyl group for a methylene group (:CH 2 ) thus forming a linear or branched substituted structure rather than a ring or can be substituted for a methylene inside of a cycloalkyl, cycloalkenyl, or cycloalkynyl ring thus forming a heterocyclic ring.
  • nitrilo (—N ⁇ ) can be substituted on benzene for one of the carbons and associated hydrogen to provide pyridine, or and oxy radical can be substituted to provide pyran.
  • unsubstituted means that no hydrogen or carbon has been replaced on an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, or aryl group.
  • the active Pd(0) catalyst was scavenged by the allyl methyl carbonate in order to generate a Pd(II) ⁇ -allyl complex and stop the catalytic process. Reformation of the Pd(0) catalyst at either a selected electrode site or another selected electrode site would require either reduction of more of the Pd(OAc) 2 reagent or reduction of the ⁇ -allyl Pd(II) complex (Hayakawa et al., Nucleosides Nucleotides, 17:441, 1988).
  • Electrode array device-based experiments were initiated by depositing aryl iodide onto the electrode array device using the same methodology employed in the earlier Wacker oxidation experiment ( FIG. 3 ) (Tesfu et al., J. Am. Chem. Soc. 126:6212, 2004). To this end, all of the electrodes on the electrode array device were utilized as cathodes in order to reduce vitamin B 12 . This effectively generated a base. The base served to catalyze an esterification reaction between the hydroxyl groups of the polysaccharide polymer coating the electrode array device and the N-hydroxysuccinimide ester of 4-iodobenzoic acid. The effect of this process was to concentrate the aryl iodide substrate near the electrodes on the electrode array device.
  • the Heck reaction was then performed by submerging the electrode array device in a 2:7:1 DMF/MeCN/H 2 O solution containing Pd(0Ac) 2 , triphenyl-phosphine, triethylamine, allyl methyl carbonate, and tetrabutyl-ammonium bromide electrolyte.
  • Selected electrodes were turned on as cathodes at a voltage of ⁇ 2.4 V (relative to a Pt auxiliary electrode as an anode) in order to generate a box pattern of electrodes on the array with a dot in the center.
  • the electrodes (Pt surface) were cycled for 0.5 sec on and then 0.1 sec off for 3 min.
  • FIG. 1 shows an expanded view of 81 of the 1028 electrodes on the electrode array device.
  • the bright spots in the figure are formed by pyrene on the electrode array device's surface and coincide perfectly with the selected or activated electrodes.
  • the dark spots are electrodes that were not activated and block the background fluorescence of the electrode array device. Therefore, the confining or scavenging agent worked well and the Heck reaction was restricted to only the selected electrode regions.

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US20060205959A1 (en) * 2005-02-22 2006-09-14 Combimatrix Corporation And Washington University Process for performing an isolated Pd(II)-mediated oxidation reaction
US20100130804A1 (en) * 2008-11-26 2010-05-27 Chevron U.S.A., Inc. Electrochemical removal of conjunct polymers from chloroaluminate ionic liquids

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US8500987B2 (en) 2010-03-19 2013-08-06 Liquid Light, Inc. Purification of carbon dioxide from a mixture of gases
US8721866B2 (en) 2010-03-19 2014-05-13 Liquid Light, Inc. Electrochemical production of synthesis gas from carbon dioxide
US8961774B2 (en) 2010-11-30 2015-02-24 Liquid Light, Inc. Electrochemical production of butanol from carbon dioxide and water
US8568581B2 (en) 2010-11-30 2013-10-29 Liquid Light, Inc. Heterocycle catalyzed carbonylation and hydroformylation with carbon dioxide
US9090976B2 (en) 2010-12-30 2015-07-28 The Trustees Of Princeton University Advanced aromatic amine heterocyclic catalysts for carbon dioxide reduction
US20140206896A1 (en) 2012-07-26 2014-07-24 Liquid Light, Inc. Method and System for Production of Oxalic Acid and Oxalic Acid Reduction Products
US10329676B2 (en) 2012-07-26 2019-06-25 Avantium Knowledge Centre B.V. Method and system for electrochemical reduction of carbon dioxide employing a gas diffusion electrode
US8444844B1 (en) 2012-07-26 2013-05-21 Liquid Light, Inc. Electrochemical co-production of a glycol and an alkene employing recycled halide
US8641885B2 (en) 2012-07-26 2014-02-04 Liquid Light, Inc. Multiphase electrochemical reduction of CO2
US9175407B2 (en) 2012-07-26 2015-11-03 Liquid Light, Inc. Integrated process for producing carboxylic acids from carbon dioxide
US20130105304A1 (en) 2012-07-26 2013-05-02 Liquid Light, Inc. System and High Surface Area Electrodes for the Electrochemical Reduction of Carbon Dioxide
WO2014043648A2 (en) * 2012-09-14 2014-03-20 Liquid Light, Inc. Heterocycle catalyzed electrochemical process

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