Gallium(III)- and Indium(III)-Containing Ionic Liquids as Highly Active Catalysts in Organic Synthesis

The chemical industry still requires development of environmentally friendly processes. Acid-catalysed chemical processes may cause environmental problems. Urgent need to replace conventional acids has forced the search for sustainable alternatives. Metal-containing ionic liquids have drawn considerable attention from scientists for many years. These compounds may exhibit very high Lewis acidity, which is usually dependent on the composition of the ionic liquid with the particular content of metal salt. Therefore, metal-containing ionic liquids have found a lot of applications and are successfully employed as catalysts, co-catalysts or reaction media in various fields of chemistry, especially in organic chemistry. Gallium(III)- and indium(III)-containing ionic liquids help to transfer the remarkable activity of metal salts into even more active and easier-to-handle forms of ionic liquids. This review highlights the wide range of possible applications and the high potential of metal-containing ionic liquids with special focus on Ga(III) and In(III), which may help to outline the framework for further development of the presented research topic and synthesis of new representatives of this group of compounds.

[1]  A. Chrobok,et al.  Silica-Based Supported Ionic Liquid-like Phases as Heterogeneous Catalysts , 2022, Molecules.

[2]  Bawadi Abdullah,et al.  Metal chloride anion based ionic liquids: synthesis, characterization and evaluation of performance in hydrogen sulfide oxidative absorption , 2022, RSC advances.

[3]  H. Roesky,et al.  Recent advances in aluminum compounds for catalysis. , 2022, European Journal of Inorganic Chemistry.

[4]  Armando Carlone,et al.  Boron-Based Lewis Acid Catalysis: Challenges and Perspectives , 2021, Catalysts.

[5]  J. Guzmán-Pantoja,et al.  Isobutane/butene alkylation reaction using ionic liquids as catalysts. Toward a sustainable industry , 2021, Molecular Catalysis.

[6]  T. Strassner,et al.  Tetrakis(pentafluoroethyl)gallate, [Ga(C2F5)4]−, Ionic Liquids , 2021, Chemistry.

[7]  Yu. V. Tomilov,et al.  GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor-Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton. , 2021, The Journal of organic chemistry.

[8]  Y. Liu,et al.  Role of aromatics in isobutane alkylation of chloroaluminate ionic liquids: Insights from aromatic − ion interaction , 2021 .

[9]  Mrityunjoy Datta Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis , 2021 .

[10]  K. K. Maniam,et al.  A Review on the Electrodeposition of Aluminum and Aluminum Alloys in Ionic Liquids , 2021, Coatings.

[11]  R. Rogers,et al.  Replacing HF or AlCl3 in the Acylation of Isobutylbenzene with Chloroaluminate Ionic Liquids , 2020 .

[12]  Rian D. Dewhurst,et al.  Boron: Its Role in Energy‐Related Processes and Applications , 2020, Angewandte Chemie.

[13]  A. K. Haghi,et al.  Green Chemistry and Sustainable Technology , 2020 .

[14]  R. Rogers,et al.  Enhanced Acidity and Activity of Aluminum/Gallium-Based Ionic Liquids Resulting from Dynamic Anionic Speciation , 2019, ACS Catalysis.

[15]  M. Swadźba-Kwaśny,et al.  Borenium Ionic Liquids as Alternative to BF3 in Polyalphaolefins (PAOs) Synthesis , 2019, ACS Sustainable Chemistry & Engineering.

[16]  S. Agarwal,et al.  Ionic liquids: Green catalysts for alkene-isoalkane alkylation , 2019, Journal of Molecular Liquids.

[17]  A. Chrobok,et al.  Highly Efficient Synthesis of Alkyl Levulinates from α-Angelica Lactone, Catalyzed with Lewis Acidic Trifloaluminate Ionic Liquids Supported on Carbon Nanotubes , 2019, ACS Sustainable Chemistry & Engineering.

[18]  S. Gan,et al.  Optimisation studies on the conversion of oil palm biomass to levulinic acid and ethyl levulinate via indium trichloride-ionic liquids: A response surface methodology approach , 2019, Industrial Crops and Products.

[19]  Xinyu Lyu,et al.  Ionic Liquids Catalyzed Friedel–Crafts Alkylation of Substituted Benzenes with CCl4 Toward Trichloromethylarenes , 2018, Catalysis Letters.

[20]  A. Chrobok,et al.  Water-Tolerant Trifloaluminate Ionic Liquids: New and Unique Lewis Acidic Catalysts for the Synthesis of Chromane , 2018, Front. Chem..

[21]  D. A. Denisov,et al.  Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry. , 2018, Journal of the American Chemical Society.

[22]  Yuming Zhou,et al.  The Catalytic Performance Study of Chloroaluminate Ionic Liquids on Long-Chain Alkenes Alkylation , 2018, Energy & Fuels.

[23]  Jacob R. Ludwig,et al.  GaCl3-Catalyzed Ring-Opening Carbonyl-Olefin Metathesis. , 2018, Organic letters.

[24]  R. Rogers,et al.  Ionic liquids for sustainable processes: Liquid metal catalysis , 2018, Current Opinion in Green and Sustainable Chemistry.

[25]  I. Krossing,et al.  Catalytic Use of Low‐Valent Cationic Gallium(I) Complexes as π‐Acids , 2018 .

[26]  Zhigang Lei,et al.  Stability, Deactivation, and Regeneration of Chloroaluminate Ionic Liquid as Catalyst for Industrial C4 Alkylation , 2017 .

[27]  S. Gan,et al.  One-pot conversion of oil palm empty fruit bunch and mesocarp fiber biomass to levulinic acid and upgrading to ethyl levulinate via indium trichloride-ionic liquids , 2017 .

[28]  N. Hosmane,et al.  Ionic Liquids: Recent Advances and Applications in Boron Chemistry , 2017 .

[29]  R. Rogers,et al.  Group IIIA Halometallate Ionic Liquids: Speciation and Applications in Catalysis , 2017 .

[30]  M. Swadźba-Kwaśny,et al.  Lewis Acidic Ionic Liquids , 2017, Topics in Current Chemistry.

[31]  Suojiang Zhang,et al.  Isobutane/butene alkylation catalyzed by ionic liquids: a more sustainable process for clean oil production , 2017 .

[32]  A. Chrobok,et al.  Borenium ionic liquids as catalysts for Diels–Alder reaction: tuneable Lewis superacids for catalytic applications , 2017 .

[33]  R. Vekariya A review of ionic liquids: Applications towards catalytic organic transformations , 2017 .

[34]  Xuan Zhang,et al.  Quantitative Characterization of Lewis Acidity and Activity of Chloroaluminate Ionic Liquids , 2016 .

[35]  A. Chrobok,et al.  Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions , 2016 .

[36]  M. Yasuda,et al.  Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides. , 2016, Chemistry.

[37]  S. Dagorne,et al.  Gallium and Indium Compounds in Homogeneous Catalysis , 2016 .

[38]  A. Chrobok,et al.  Exceptional activity of gallium(III) chloride and chlorogallate(III) ionic liquids for Baeyer–Villiger oxidation , 2016 .

[39]  C. Pomelli,et al.  Alkylation of Methyl Linoleate with Propene in Ionic Liquids in the Presence of Metal Salts , 2015, Molecules.

[40]  J. Holbrey,et al.  Lewis Superacidic Ionic Liquids with Tricoordinate Borenium Cations. , 2015, Angewandte Chemie.

[41]  A. Chrobok,et al.  Friedel–Crafts alkylation catalysed by GaCl3-based liquid coordination complexes , 2015 .

[42]  M. Swadźba-Kwaśny,et al.  Liquid coordination complexes: a new class of Lewis acids as safer alternatives to BF3 in synthesis of polyalphaolefins , 2015 .

[43]  Chunming Xu,et al.  Identification of acidic species in chloroaluminate ionic liquid catalysts , 2014 .

[44]  Wei Zhang,et al.  Recyclable Gallium(III) Triflate-Catalyzed [4 + 3] Cycloaddition for Synthesis of 2,4-Disubstituted-3H-benzo[b][1,4]diazepines. , 2014 .

[45]  Pei-He Li,et al.  Ionic liquid supported on magnetic nanoparticles as highly efficient and recyclable catalyst for the synthesis of β-keto enol ethers , 2014 .

[46]  A. Riisager,et al.  Supported ionic liquids : fundamentals and applications , 2014 .

[47]  J. Holbrey,et al.  Halometallate ionic liquids--revisited. , 2014, Chemical Society reviews.

[48]  T. O’Sullivan,et al.  Recent applications of gallium and gallium halides as reagents in organic synthesis , 2013 .

[49]  Ying Liang,et al.  Ligand-free indium(III)-catalyzed Heck reaction , 2013 .

[50]  Faiz Ullah Shah,et al.  Boron in Tribology: From Borates to Ionic Liquids , 2013, Tribology Letters.

[51]  S. Muthusubramanian,et al.  Indium Trichloride Catalyzed Regioselective Synthesis of Substituted Pyrroles in Water. , 2013 .

[52]  H. Khavasi,et al.  [Bmim][InCl4]-Catalyzed Addition of Hydrazones to β-Diketones: An Efficient Regioselective Synthesis of Pyrazoles and Pyrazole-Fused Cyclohexanones , 2013, Synlett.

[53]  R. Hughes,et al.  Gallium(III)-Catalyzed Three-Component [4 + 3] Cycloaddition Reactions. , 2013 .

[54]  G. Srinivasan,et al.  Buffered chlorogallate(III) ionic liquids and electrodeposition of gallium films. , 2013, Physical chemistry chemical physics : PCCP.

[55]  Shiguo Zhang,et al.  Highly efficient trimerization of isobutene over silica supported chloroaluminate ionic liquid using C4 feed , 2013 .

[56]  S. Luo,et al.  Catalytic Nazarov reaction of aryl vinyl ketones via binary acid strategy. , 2013, The Journal of organic chemistry.

[57]  B. Reddy,et al.  Gallium(III)-Catalyzed Tandem Cycloisomerization/Friedel—Crafts Alkylation: A Facile Synthesis of 2,5-Disubstituted Furans. , 2012 .

[58]  M. Yasuda,et al.  Gallium tribromide catalyzed coupling reaction of alkenyl ethers with ketene silyl acetals. , 2012, Angewandte Chemie.

[59]  Yu. V. Tomilov,et al.  Unexpected formation of 4-arylcyclopentane-1,1,3,3-tetracarboxylates in GaCl3-catalyzed reaction of 2-arylcyclopropane-1,1-dicarboxylates with tetrasubstituted 1-pyrazolines , 2012 .

[60]  B. Reddy,et al.  Gallium(III)-catalyzed tandem cycloisomerization/Friedel–Crafts alkylation: a facile synthesis of 2,5-disubstituted furans , 2012 .

[61]  G. Olah,et al.  Gallium(III) triflate: an efficient and a sustainable Lewis acid catalyst for organic synthetic transformations. , 2012, Accounts of chemical research.

[62]  G. Srinivasan,et al.  Electrochemical synthesis of indium(0) nanoparticles in haloindate(III) ionic liquids. , 2012, ChemSusChem.

[63]  D. Macfarlane,et al.  Understanding the effect of the C2 proton in promoting low viscosities and high conductivities in imidazolium-based ionic liquids: part I. Weakly coordinating anions. , 2011, The journal of physical chemistry. B.

[64]  Jomy Joseph,et al.  Efficient Synthesis of 3,4-Dihydropyrimidinones in 1-n-Butyl-3-methylimidazolium Tetrachloroindate (BMI·InCl4) , 2011 .

[65]  K. R. Seddon,et al.  Oligomerisation of linear 1-olefins using a chlorogallate(III) ionic liquid , 2011 .

[66]  Gebo Pan,et al.  Nanoscale Electrodeposition of Ga on Au(111) from Ionic Liquids , 2011 .

[67]  Jiang-Jen Lin,et al.  Preparation of high energy fuel JP-10 by acidity-adjustable chloroaluminate ionic liquid catalyst , 2011 .

[68]  K. R. Seddon,et al.  Chlorometallate(III) ionic liquids as Lewis acidic catalysts--a quantitative study of acceptor properties. , 2010, Dalton transactions.

[69]  Hui-jing Li,et al.  A gallium-catalyzed cycloisomerization/Friedel-Crafts tandem. , 2010, The Journal of organic chemistry.

[70]  A. Leipertz,et al.  The role of the C2 position in interionic interactions of imidazolium based ionic liquids: a vibrational and NMR spectroscopic study. , 2010, Physical chemistry chemical physics : PCCP.

[71]  G. Srinivasan,et al.  Speciation of chloroindate(III) ionic liquids. , 2010, Dalton transactions.

[72]  H. Gunaratne,et al.  Chloroindate(III) ionic liquids as catalysts for alkylation of phenols and catechol with alkenes , 2010 .

[73]  G. Srinivasan,et al.  Speciation of Chlorometallate Ionic Liquids Based on Gallium(III) and Indium(III) , 2010 .

[74]  M. Yasuda,et al.  Indium-Catalyzed Coupling Reaction Between Silyl Enolates and Alkyl Chlorides or Alkyl Ethers. , 2009 .

[75]  Jiang-Jen Lin,et al.  Isomerization of exo-tetrahydrodicyclopentadiene to adamantane using an acidity-adjustable chloroaluminate ionic liquid , 2009 .

[76]  Haihong Zhao,et al.  Preparation and catalytic activity of periodic mesoporous organosilica incorporating Lewis acidic chloroindate(III) ionic liquid moieties , 2009 .

[77]  Guozhen Gong,et al.  Highly efficient procedure for the synthesis of biodiesel from soybean oil using chloroaluminate ionic liquid as catalyst , 2009 .

[78]  R. Luque,et al.  Activity of Gallium and Aluminum SBA-15 materials in the Friedel–Crafts alkylation of toluene with benzyl chloride and benzyl alcohol , 2008 .

[79]  Chunming Xu,et al.  Isomerization of n-Pentane Catalyzed by Acidic Chloroaluminate Ionic Liquids , 2008 .

[80]  Douglas R. MacFarlane,et al.  Electrodeposition from Ionic Liquids , 2008 .

[81]  M. Maase Industrial Applications of Ionic Liquids , 2008 .

[82]  M. White,et al.  Super acidic ionic liquids for arene carbonylation derived from dialkylimidazolium chlorides and MCl3 (M = Al, Ga, or In) , 2007 .

[83]  Christopher Hardacre,et al.  Catalysis in ionic liquids. , 2007, Chemical reviews.

[84]  Hongwei Zhou,et al.  GaCl3-Catalyzed Chloroacylation of Alkynes: A Simple, Convenient and Efficient Method to β-Chlorovinyl Ketones. , 2007 .

[85]  Prashant Kumar,et al.  Production of alkylated gasoline using ionic liquids and immobilized ionic liquids , 2006 .

[86]  J. Dupont,et al.  Addition of activated olefins to cyclic N-acyliminium ions in ionic liquids , 2006 .

[87]  L. Kollár,et al.  Palladium catalysed hydroethoxycarbonylation in imidazolium-based ionic liquids , 2006 .

[88]  Anilesh Kumar,et al.  Recent Applications of Chloroaluminate Ionic Liquids in Promoting Organic Reactions , 2006 .

[89]  Y. J. Kim,et al.  Microwave-assisted preparation of 1-butyl-3-methylimidazolium tetrachlorogallate and its catalytic use in acetal formation under mild conditions , 2005 .

[90]  Y. J. Kim,et al.  Tetrahaloindate(III)-based ionic liquids in the coupling reaction of carbon dioxide and epoxides to generate cyclic carbonates: H-bonding and mechanistic studies. , 2005, The Journal of organic chemistry.

[91]  J. Yadav,et al.  Gallium(III) Halide Promoted Synthesis of 1,3,5‐Triaryl‐1,5‐dihalo‐1,4‐pentadienes. , 2005 .

[92]  Y. J. Kim,et al.  Microwave-assisted preparation of imidazolium-based tetrachloroindate(III) and their application in the tetrahydropyranylation of alcohols , 2005 .

[93]  D. Rooney,et al.  Chloroindate(III) ionic liquids: recyclable media for Friedel-Crafts acylation reactions. , 2005, Chemical communications.

[94]  J. Yadav,et al.  Gallium(III) halide-catalyzed coupling of indoles with phenylacetylene: synthesis of bis(indolyl)phenylethanes , 2004 .

[95]  S. Murai,et al.  A GaCl3‐Catalyzed [4 + 1] Cycloaddition of α,β‐Unsaturated Carbonyl Compounds and Isocyanides Leading to Unsaturated γ‐Lactone Derivatives. , 2003 .

[96]  Robin D. Rogers,et al.  Ionic Liquids--Solvents of the Future? , 2003, Science.

[97]  S. Murai,et al.  A GaCl3-Catalyzed [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds and Isocyanides Leading to Unsaturated γ-Lactone Derivatives , 2003 .

[98]  W. Hölderich,et al.  Immobilisation of ionic liquids on solid supports , 2002 .

[99]  M. Salunkhe,et al.  Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation , 2002 .

[100]  W. Hölderich,et al.  Immobilisation of chloroaluminate ionic liquids on silica materials , 2000 .

[101]  Viktor Gutmann,et al.  The Donor-Acceptor Approach to Molecular Interactions , 1978 .

[102]  H. Jung,et al.  Cationic aluminum, gallium, and indium complexes in catalysis , 2021 .

[103]  Commercial Applications of Ionic Liquids , 2020 .

[104]  J. Coutinho,et al.  Immobilization of Ionic Liquids, Types of Materials, and Applications , 2019, Encyclopedia of Ionic Liquids.

[105]  Eric Mayer,et al.  Ionic Liquids In Synthesis , 2016 .

[106]  J. Dupont,et al.  Ionic Liquids (ILs) in Organometallic Catalysis , 2015 .

[107]  Suojiang Zhang,et al.  Fundamentals of Ionic Liquids , 2014 .

[108]  Guo-ying Zhao,et al.  Chlorogallate(III) ionic liquids: Synthesis, acidity determination and their catalytic performances for isobutane alkylation , 2012, Science China Chemistry.

[109]  刘哲,et al.  FeCl3- and GaCl3-Catalyzed Dehydrative Coupling Reaction of Chromone-Derived Morita-Baylis-Hillman Alcohols with Terminal Alkynes , 2011 .

[110]  F. Wei,et al.  Crystal structure of room-temperature ionic liquid 1-butyl-isoquinolinium gallium tetrachloride [(BIQL)GaCl4] , 2008 .

[111]  K. R. Seddon,et al.  Applications of ionic liquids in the chemical industry. , 2008, Chemical Society reviews.

[112]  Y. Chauvin,et al.  Catalytic dimerization of alkenes by nickel complexes in organochloroaluminate molten salts , 1990 .