2002 Progress Report: Forming Carbon-Carbon Bonds in Water and Other Alternative Media

EPA Grant Number: R828129
Title: Forming Carbon-Carbon Bonds in Water and Other Alternative Media
Investigators: Li, Chao-Jun
Institution: Tulane University of Louisiana
EPA Project Officer: Hahn, Intaek
Project Period: June 1, 2000 through May 31, 2003 (Extended to September 24, 2004)
Project Period Covered by this Report: June 1, 2001 through May 31, 2002
Project Amount: $310,000
RFA: Technology for a Sustainable Environment (1999) RFA Text |  Recipients Lists
Research Category: Sustainability , Pollution Prevention/Sustainable Development

Objective:

The long-term objective of this research project is to develop various environmentally friendly chemical syntheses using water, liquid CO2, and ionic liquid as nonpolluting solvents. The specific objective during this funding period is to study new carbon-carbon bond formation reactions that do not use anhydrous organic solvent, avoids the use of protection-deprotections, is applicable to large-scale industry operation, and has a reduced impact on environment due to the use of catalytic amount of metal and/or in-process recycling.

Progress Summary:

Metal-mediated carbon-carbon bond formation is one of the most important fundamental reactions in organic chemistry and is widely used in various chemical and pharmaceutical processes. Traditionally, they are conducted in anhydrous organic solvents, are air-sensitive, and are potentially explosive. The present study investigates the scope, mechanism, and synthetic application of metal-mediated reactions through the use of water solvent. During this period, we have investigated and succeeded metal-mediated carbon-carbon bond formations involving SP3 hybridized C-X bonds, SP2 hybridized C-X bonds, and SP hybridized C-X bonds. The method saves synthetic steps by avoiding many protection and deprotection processes and contributes to overall synthetic efficiency and a reduction in organic emission. Additional research is planned to transform the reaction into a catalytic process. Additionally, the uses of liquid CO2 and ionic liquid as nonpolluting solvent for carbon-carbon bond formations also have been investigated during this period. A Barbier-type reaction in liquid CO2 and a novel synthesis of tetrahydropyran derivatives have been synthesized in ionic liquids for the first time. These methods provided cleaner approaches for synthesizing complex pharmaceuticals (currently, the industry that generates the largest amount of waste/per Kg of products).

During the second budget year, we have further evaluated metal-mediated carbon-carbon bond formations and related reactions in the synthesis of C-glycoside-type natural products. Research activities have been focused on the syntheses of natural products (+)-bergenin. Substantial progresses have been made on the syntheses of all these biologically important compounds. We have developed a novel one-step process that can be used to generate tetrahydropyranols that will have important applications in the synthesis of C-glycoside natural products. We also have developed a palladium-catalyzed formation of carbon-carbon bonds in air and water. Such results have both theoretical and practical values.

During this year, 10 graduate students, 4 postdoctoral students, and 2 undergraduate students have benefited either directly or indirectly from the support of this project. These students have gained valuable experience in organic synthesis and structural characterizations.

During the first budget year, the principal investigator (PI) has further polished the short precourse, entitled "The World of Organic Chemistry." The course was scheduled before the regular organic chemistry text. At the end of the course, each student wrote an essay with the title: "Chemistry and Me." All the students were very enthusiastic about this part of the course with well-written essays. The PI also has added new experiments and variation to the public outreach program. The PI conducted two science demonstrations in a public elementary school. All the students were extremely interested in the demonstration and in chemistry. A graduate student also was involved in the outreach.

Future Activities:

We will continue our work towards the project objectives. A major objective is to further greening such reactions in water, liquid CO2, and ionic liquids.


Journal Articles on this Report : 56 Displayed | Download in RIS Format

Other project views: All 86 publications 60 publications in selected types All 56 journal articles
Type Citation Project Document Sources
Journal Article Chen L, Li C-J. Domino reaction of anilines with 3,4-dihydro-2H-pyran catalyzed by cation-exchange resin in water: an efficient synthesis of 1,2,3,4-tetrahydroquinoline derivatives. Green Chemistry 2003;5(5):627-629. R828129 (2002)
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  • Journal Article Chen L, Li Z, Li C-J. Indium-mediated domino reaction of nitroarenes with 2,3-dihydrofuran in water: an efficient synthesis of 1,2,3,4-tetrahydroquinoline derivatives. Synlett 2003;(5):732-734. R828129 (2002)
    R826740 (Final)
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  • Journal Article Chen L, Li C-J. The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones. Chemical Communications 2004;(20):2362-2364. R828129 (2002)
    R831662 (Final)
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  • Journal Article Chen L, Li C-J. A remarkably efficient coupling of acid chlorides with alkynes in water. Organic Letters 2004;6(18):3151-3153. R828129 (2002)
    R831662 (Final)
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  • Journal Article Ding R, Ge CS, Chen YJ, Wang D, Li CJ. Rhodium-catalyzed reactions of arylbismuth and aryllead reagents with a chiral glyoxylate hydrate in air and water: water-promoted diastereoselectivity enhancement. Tetrahedron Letters 2002;43(43):7789-7791. R828129 (2002)
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  • Journal Article Ding R, Zhang HB, Chen YJ, Liu L, Wang D, Li CJ. In(OTf)3-catalyzed Friedel-Crafts reaction of aromatic compounds with methyl trifluoropyruvate in water. Synlett 2004;(3):555-557. R828129 (2002)
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  • Journal Article Ding R, Zhao CH, Chen YJ, Liu L, Wang D, Li CJ. Rhodium-catalyzed and sonication-accelerated addition of aryltin and aryllead reagents to imines in air and water. Tetrahedron Letters 2004;45(14):2995-2998. R828129 (2002)
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  • Journal Article Huang TS, Li CJ. Palladium-catalyzed coupling of aryl halides with arylhalosilanes in air and water. Tetrahedron Letters 2002;43(3):403-405. R828129 (2002)
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  • Journal Article Huang T, Keh CCK, Li CJ. Synthesis of α-amino acid derivatives and amines via activation of simple alkyl halides by zinc in water. Chemical Communications 2002;(20):2440-2441. R828129 (2002)
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  • Journal Article Huang T, Li C-J. Synthesis of α-amino γ-lactone via a novel tandem three-component reaction of alkenes, glyoxylates and amines. Tetrahedron Letters 2000;41(50):9747-9751. R828129 (2002)
    R822668 (Final)
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  • Journal Article Huang T, Meng Y, Venkatraman S, Wang D, Li C-J. Remarkable electronic effect on rhodium-catalyzed carbonyl additions and conjugated additions with arylmetallic reagents. Journal of the American Chemical Society 2001;123(30):7451-7452. R828129 (2002)
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  • Journal Article Huang T-S, Li C-J. Novel synthesis of α-amino acids via catalysis in air and water. Organic Letters 2001;3(13):2037-2039. R828129 (2002)
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  • Journal Article Huang T-S, Li C-J. Conjugate addition of arylsilanes to unsaturated carbonyl compounds catalyzed by rhodium in air and water. Chemical Communications 2001;(22):2348-2349. R828129 (2002)
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  • Journal Article Jiang N, Hu Q, Reid CS, Lu Y, Li C-J. A novel palladium-catalyzed coupling of epoxides with allyl bromide mediated by indium(i) chloride: a cascade epoxide rearrangement-carbonyl allylation. Chemical Communications 2003;(18):2318-2319. R828129 (2002)
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  • Journal Article Ju Y, Li C-J, Varma R. Microwave-assisted Cu (I) catalyzed solvent-free three component coupling of aldehyde, alkyne and amine. QSAR & Combinatorial Science 2004;23(10):891-894. R828129 (2002)
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  • Journal Article Keh CCK, Wei CM, Li C-J. The Barbier-Grignard-type carbonyl alkylation using unactivated alkyl halides in water. Journal of the American Chemical Society 2003;125(14):4062-4063. R828129 (2002)
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  • Journal Article Keh CCK, Namboodiri VV, Varma RS, Li CJ. Direct formation of tetrahydropyranols via catalysis in ionic liquid. Tetrahedron Letters 2002;43(28):4993-4996. R828129 (2002)
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  • Journal Article Keh CCK, Li CJ. Direct formation of 2,4-disubstituted tetrahydropyranols in water mediated by an acidic solid resin. Green Chemistry 2003;5(1):80-81. R828129 (2002)
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  • Journal Article Li C-J, Wei CM. Highly efficient Grignard-type imine additions via C-H activation in water and under solvent-free conditions. Chemical Communications 2002;(3):268-269. R828129 (2002)
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  • Journal Article Li C-J. Quasi-nature catalysis: developing C-C bond formations catalyzed by late transition metals in air and water. Accounts of Chemical Research 2002;35(7):533-538. R828129 (2002)
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  • Journal Article Li C-J. Developing metal-mediated and catalyzed reactions in air and water. Green Chemistry 2002;4(1):1-4. R828129 (2002)
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  • Journal Article Li C-J. Suzuki reaction takes a “naked hot bath”: coupling in high‐temperature water without transition metals. Angewandte Chemie International Edition 2003;42(40):4856-4858. R828129 (2002)
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  • Journal Article Li HJ, Tian HY, Chen YJ, Wang D, Li CJ. Novel chiral gallium Lewis acid catalysts with semi-crown ligands for aqueous asymmetric Mukaiyama aldol reactions. Chemical Communications 2002;(24):2994-2995. R828129 (2002)
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  • Journal Article Li J, Li C-J. Synthesis of tetrahydropyran derivatives via a novel indium trichloride mediated cross-cyclization between epoxides and homoallyl alcohols. Tetrahedron Letters 2001;42(5):793-796. R828129 (2002)
    R822668 (Final)
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  • Journal Article Li Z, Zhang J, Li C-J. InCl3-catalyzed reaction of aromatic amines with cyclic hemiacetals in water: facile synthesis 1,2,3,4-tetrahydroquinoline derivatives. Tetrahedron Letters 2003;44(1):153-156. R828129 (2002)
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  • Journal Article Li Z, Wei C, Chen L, Varma RS, Li C-J. Three-component coupling of aldehyde, alkyne, and amine catalyzed by silver in ionic liquid. Tetrahedron Letters 2004;45(11):2443-2446. R828129 (2002)
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  • Journal Article Li Z, Li C-J. CuBr-catalyzed efficient alkynylation of sp3 C−H bonds adjacent to a nitrogen atom. Journal of the American Chemical Society 2004;126(38):11810-11811. R828129 (2002)
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  • Journal Article Matsumura Y, Onomura O, Suzuki H, Furukubo S, Maki T, Li C-J. Indium-mediated nucleophilic substitution reaction of β,γ-unsaturated α-methoxypiperidine derivative in water. Tetrahedron Letters 2003;44(29):5519-5522. R828129 (2002)
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  • Journal Article Ning W, Li C-J, Kaminski N, Feghali-Bostwick CA, Alber SM, Di YP, Otterbein SL, Song R, Hayashi S, Zhou Z, Pinsky DJ, Watkins SC, Pilewski JM, Sciurba FC, Peters DG, Hogg JC, Choi AMK. Comprehensive gene expression profiles reveal pathways related to the pathogenesis of chronic obstructive pulmonary disease. Proceedings of the National Academy of Sciences of the United States of America 2004;101(41):14895-14900. R828129 (2002)
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  • Journal Article Tian H-Y, Li H-J, Chen Y-J, Wang D, Li C-J. Development of highly effective encapsulating surfactants for Mukaiyama aldol reactions in water. Industrial & Engineering Chemistry Research 2002;41(18):4523-4527. R828129 (2002)
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  • Journal Article Tian H-Y, Chen Y-J, Wang D, Bu Y-P, Li C-J. The effects of aromatic and aliphatic anionic surfactants on Sc(OTf)3-catalyzed Mukaiyama aldol reaction in water. Tetrahedron Letters 2001;42(10):1803-1805. R828129 (2002)
    R822668 (Final)
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  • Journal Article Venkatraman S, Li C-J. Carbon-carbon bond formation via palladium-catalyzed reductive coupling in air. Organic Letters 1999;1(7):1133-1135. R828129 (2002)
    R822668 (Final)
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  • Journal Article Venkatraman S, Li C-J. Rhodium catalyzed conjugated addition of unsaturated carbonyl compounds by triphenylbismuth in aqueous media and under an air atmosphere. Tetrahedron Letters 2001;42(5):781-784. R828129 (2002)
    R822668 (Final)
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  • Journal Article Venkatraman S, Meng Y, Li C-J. Quasi-nature catalysis: conjugated addition of unsaturated carbonyl compounds with aryl and vinyltin reagents catalyzed by rhodium in air and water. Tetrahedron Letters 2001;42(27):4459-4462. R828129 (2002)
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  • Journal Article Venkatraman S, Huang T, Li CJ. Carbon-carbon bond formation via palladium-catalyzed reductive coupling of aryl halides in air and water. Advanced Synthesis & Catalysis 2002;344(3-4):399-405. R828129 (2002)
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  • Journal Article Viswanathan GS, Wang MW, Li C-J. A highly regioselective synthesis of polysubstituted naphthalene derivatives through gallium trichloride catalyzed alkyne--aldehyde coupling. Angewandte Chemie-International Edition 2002;41(12):2138-2141. R828129 (2002)
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  • Journal Article Viswanathan GS, Li CJ. A highly stereoselective, novel coupling reaction between alkynes and aldehydes. Tetrahedron Letters 2002;43(9):1613-1615. R828129 (2002)
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  • Journal Article Viswanathan GS, Li CJ. Synthesis of naphthalene derivatives via a novel gallium trichloride catalyzed cross-coupling of epoxides with alkynes. Synlett 2002;(9):1553-1555. R828129 (2002)
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  • Journal Article Wang M, Li C-J. Aldol reaction via in situ olefin migration in water. Tetrahedron Letters 2002;43(19):3589-3591. R828129 (2002)
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  • Journal Article Wang M, Yang X-F, Li C-J. Ruthenium-catalyzed tandem olefin migration/aldol and Mannich-type reactions in water and protic solvents. European Journal of Organic Chemistry 2003;(6):998-1003. R828129 (2002)
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  • Journal Article Wang Z, Yuan S, Li C-J. Gallium-mediated allylation of carbonyl compounds in water. Tetrahedron Letters 2002;43(29):5097-5099. R828129 (2002)
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  • Journal Article Wei CM, Li CJ. Grignard type reaction via C–H bond activation in water. Green Chemistry 2002;4(1):39-41. R828129 (2002)
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  • Journal Article Wei C, Li C-J. A highly efficient three-component coupling of aldehyde, alkyne, and amines via C−H activation catalyzed by gold in water. Journal of the American Chemical Society 2003;125(32):9584-9585. R828129 (2002)
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  • Journal Article Wei C, Li Z, Li C-J. The first silver-catalyzed three-component coupling of aldehyde, alkyne, and amine. Organic Letters 2003;5(23):4473-4475. R828129 (2002)
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  • Journal Article Wei CM, Li CJ. Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene. Journal of the American Chemical Society 2002;124(20):5638-5639. R828129 (2002)
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  • Journal Article Wei W, Keh CCK, Li C-J, Varma RS. Water as a reaction medium for clean chemical processes. Clean Technologies and Environmental Policy 2004;6(4):250-257. R828129 (2002)
    R831662 (Final)
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  • Journal Article Wen C-J, Xue B, Qin W-X, Yu M, Zhang M-Y, Zhao D-H, Gao X, Gu J-R, Li C-J. hNRAGE, a human neurotrophin receptor interacting MAGE homologue, regulates p53 transcriptional activity and inhibits cell proliferation. FEBS Letters 2004;564(1-2):171-176. R828129 (2002)
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  • Journal Article Wu W, Li C-J. A highly regio- and stereoselective transition metal-catalyzed hydrosilylation of terminal alkynes under ambient conditions of air, water, and room temperature. Chemical Communications 2003;(14):1668-1669. R828129 (2002)
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  • Journal Article Xia WS, Schmehl RH, Li CJ, Mague JT, Luo CP, Guldi DM. Chemosensors for lead(II) and alkali metal ions based on self-assembling fluorescence enhancement (SAFE). Journal of Physical Chemistry B 2002;106(4):833-843. R828129 (2002)
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  • Journal Article Yang X-F, Mague JT, Li C-J. Diastereoselective synthesis of polysubstituted tetrahydropyrans and thiacyclohexanes via indium trichloride mediated cyclizations. Journal of Organic Chemistry 2001;66(3):739-747. R828129 (2002)
    R822668 (Final)
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  • Journal Article Yang X-F, Wang M, Varma RS, Li C-J. Aldol- and Mannich-type reactions via in situ olefin migration in ionic liquid. Organic Letters 2003;5(5):657-660. R828129 (2002)
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  • Journal Article Yao X, Li C-J. Highly efficient addition of activated methylene compounds to alkenes catalyzed by gold and silver. Journal of the American Chemical Society 2004;126(22):6884-6885. R828129 (2002)
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  • Journal Article Yu Y-Y, Chen Y, Dai G, Chen J, Sun X-M, Wen C-J, Zhao D-H, Chang DC, Li C-J. The association of calmodulin with central spindle regulates the initiation of cytokinesis in HeLa cells. The International Journal of Biochemistry & Cell Biology 2004;36(8):1562-1572. R828129 (2002)
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  • Journal Article Zhang JH, Wei CM, Li CJ. Cu(I)Br mediated coupling of alkynes with N-acylimine and N-acyliminium ions in water. Tetrahedron Letters 2002;43(33):5731-5734. R828129 (2002)
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  • Journal Article Zhang JH, Li CJ. InCl3-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water:a highly efficient synthesis of new 1,2,3,4-tetrahydroquinoline derivatives. Journal of Organic Chemistry 2002;67(11):3969-3971. R828129 (2002)
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  • Journal Article Zhang Y, Li C-J. Microwave-assisted direct addition of cycloethers to alkynes. Tetrahedron Letters 2004;45(41):7581-7584. R828129 (2002)
    R831662 (Final)
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  • Supplemental Keywords:

    water, metals, chemicals, solvents, organics, green chemistry, alternatives, sustainable development, clean technology, waste reduction, waste minimization, environmental chemistry, industry, petroleum, chemical, pharmaceutical., RFA, Scientific Discipline, Air, Sustainable Industry/Business, Chemical Engineering, air toxics, cleaner production/pollution prevention, Environmental Chemistry, Sustainable Environment, Technology for Sustainable Environment, water-based solvent, cleaner production, waste minimization, waste reduction, chemical waste, environmentally benign solvents, carbon bonds, anhydrous organic solvents, treatment, organic chemicals, pollution prevention, environmentally-friendly chemical synthesis, green chemistry

    Relevant Websites:

    http://www.tulane.edu/~chemstry/Li.html Exit

    Progress and Final Reports:

    Original Abstract
  • 2000
  • 2001
  • 2003
  • Final