Fluorous Lewis acids and phase transfer catalysts

Molecular Diversity

Volumn 13, Issue 2, 2009, Pages 209-239

  Cai, Chun ^a   Yi, Wen Bin ^a   Zhang, Wei ^b   Shen, Ming Gui ^a   Hong, Mei ^a   Zeng, Li Yan ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

Fluorous biphasic catalysis; Fluorous crown ethers; Fluorous Lewis acids; Fluorous onium salts; Fluorous phase transfer catalysis; Metal bis(perfluorooctanesulfonyl)amides; Metal perfluorooctanesulfonates

Indexed keywords

AMIDE; BENZIMIDAZOLE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; CROWN ETHER DERIVATIVE; FLUOROCARBON; IMIDAZOLE DERIVATIVE; LEWIS ACID; PERFLUOROOCTANESULFONIC ACID; QUATERNARY AMMONIUM DERIVATIVE; XANTHENE DERIVATIVE;

ALDOL REACTION; ALKYLATION; BAEYER VILLIGER REACTION; BAYLIS HILLMAN REACTION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ESTERIFICATION; FRIEDEL CRAFTS REACTION; KNOEVENAGEL CONDENSATION; MANNICH REACTION; NITRATION; OXIDATION; PHASE SEPARATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SONOGASHIRA REACTION; SUZUKI REACTION; SYNTHESIS;

ALKANESULFONIC ACIDS; AMIDES; CATALYSIS; FLUORINE; FLUOROCARBONS; ORGANOMETALLIC COMPOUNDS; PHASE TRANSITION;

EID: 67349113870     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-008-9103-y     Document Type: Review

References (210)

1. DW Zhu 1993 A novel reaction medium: perfluorocarbon fluids Synthesis 10 953 954 10.1055/s-1993-25975
2. M Kidwai 2006 Green chemistry trends toward sustainability Pure Appl Chem 78 1983 1992
3. IT Horváth J Rábai 1994 Facile catalyst separation without water: fluorous biphase hydyoformylation of olefins Science 266 72 75 10.1126/science.266.5182.72
4. Horváth IT, Rábai J (1995) Exxon research and engineering comp. US 5463082
5. Yamamoto H (2000) Lewis acids in organic synthesis. Wiley-VCH, New York
6. Gladysz JA, Curran DP, Horváth IT (2004) Handbook of fluorous chemistry. Wiley-VCH, Weinheim
7. A Yoshida XH Hao O Yamazaki J Nishikido 2006 Development of fluorous Lewis acid-catalyzed reactions Molecules 11 627 640 10.3390/11080627
8. Yi WB (2006) Organic synthesis in fluorous biphasic system. Ph.D. thesis, Nanjing, China, 2006
9. Starks CM, Liotta CL, Halpern M (1994) Phase transfer catalysis. Chapman & Hall, New York
10. GD Yadav 2004 Insight into green phase transfer catalysis Top Catal 29 145 161 10.1023/B:TOCA.0000029797.93561.cd
11. SL Desikan K Doraiswamy 1995 The diffusion-reaction problem in triphase catalysis Ind Eng Chem Res 34 3524 3537 10.1021/ie00037a041 (and references therein)
12. Reeves RL (1966) Chemistry of carbonyl group. Wiley Intersciences, New York
13. A Clerici N Pastori O Porta 2005 Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus Aldol and direct Mannich-type syn-diastereoselective condensation J Org Chem 70 4174 4176 10.1021/jo048279f (and references therein)
14. K Irie K Watanabe 1980 Aldol condensations with metal(II) complex catalysts Bull Chem Soc Jpn 53 1366 1371 10.1246/bcsj.53.1366
15. WB Yi C Cai 2005 Aldol condensations of aldehydes and ketones catalyzed by rare earth (III) perfluorooctane sulfonates in fluorous solvents J Fluor Chem 126 1553 1558 10.1016/j.jfluchem.2005.09.004
16. Olah GA (1964) Friedel-Crafts and related reaction, vol III. part I. Interscience, New York
17. M Shi SC Cui 2002 Friedel-Crafts reaction catalyzed by perfluorinated rare earth metals J Fluor Chem 116 143 147 10.1016/S0022-1139(02)00126-4
18. WB Yi C Cai 2005 Rare earth (III) perfluorooctanesulfonates catalyzed Friedel-Crafts alkylation in fluorous biphase system J Fluor Chem 126 831 833 10.1016/j.jfluchem.2005.03.010
19. S Kobayashi S Iwamoto 1998 Catalytic Friedel-Crafts acylation of benzene, chlorobenzene, and fluobenzene using a novel catalyst system, hafnium triflate and trifluoromethanesulfonic acid Tetrahedron Lett 39 4697 4700 10.1016/S0040-4039(98)00881-8
20. WB Yi C Cai 2005 Rare earth (III) perfluorooctane sulfonates and perfluorooctanesulfonic acid in fluorous solvents: novel and recyclable catalytic systems for Friedel-Crafts acylation of unactivated benzenes J Fluor Chem 126 1191 1195 10.1016/j.jfluchem.2005.05.008
21. Johnson JR (1942) Organic react, vol 1. Wiley, New York, 210 p
22. WB Yi YQ Yin C Cai 2007 Ytterbium perfluooctanesulfonate-catalyzed Knoevenagel condensation in a fluorous biphasic system Org Prep Proced Int 39 71 75
23. YQ Cai YL Peng GH Song 2006 Amino-functionalized ionic liquid as an efficient and recyclable catalyst for Knoevenagel reactions in water Catal Lett 109 61 64 10.1007/s10562-006-0057-3 (and references therein)
24. D Basavaiah AJ Rao T Satyanarayana 2003 Advances in the Baylis-Hillman reaction and applications Chem Rev 103 811 892 10.1021/cr010043d (and references therein)
25. SH Zhao HR Zhang LH Feng ZB Chen 2006 Pyridinium ionic liquids-accelerated amine-catalyzed Morita-Baylis-Hillman reaction J Mol Catal Chem 258 251 256 10.1016/j.molcata.2006.05.032 (and references therein)
26. VK Aggarwal A Mereu GJ Tarver R McCague 1998 Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction J Org Chem 63 7183 7189 10.1021/jo980421n
27. VK Aggarwal A Mereu 1999 Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications Chem Commun 22 2311 2312 10.1039/a907754e
28. D Balan H Adolfsson 2001 Selective formation of α-methylene-β- amino acid derivatives through the aza version of the Baylis-Millman reaction J Org Chem 66 6498 6501 10.1021/jo0158635
29. WB Yi C Cai X Wang 2007 A novel ytterbium/perfluoalkylated-pyridine catalyst for Baylis-Hillman reaction in a fluorous biphasic system J Fluor Chem 128 919 924 10.1016/j.jfluchem.2007.03.017
30. Rosini G (1991) In: Trost BM, Fleming I, Heathcock CH (eds) Comprehensive organic synthesis. Pergamon, New York, pp 321-340
31. I Kudyba J Raczko Z Urbaczyk-Lipkowska J Jurczak 2004 Highly diastereoselective Henry reaction of nitro compounds with chiral derivatives of glyoxylic acid Tetrahedron 60 4807 4820 10.1016/j.tet.2004.04.005 (and references cited therein)
32. CS Gan GY Lai ZH Zhang ZY Wang 2006 Efficient and enantioselective nitroaldol reaction catalyzed by copper Schiff-base complexes Tetrahedron: Asymmetry 17 725 728 (and reference therein)
33. BM Trost 1991 The atom economy-a search for synthetic efficiency Science 254 1471 1477 10.1126/science.1962206
34. BM Trost 1985 Sculpting horizons in organic chemistry Science 227 908 916 10.1126/science.3969569
35. CL Zhou QY Zhou ZY Wang 2003 Henry reaction in aqueous media: chemoselective addition of aldehydes Chin Chem Lett 14 355 358
36. WB Yi X Wang C Cai 2007 Nitroaldol reaction in fluorous media: an important improvement of the chemoselective addition of aldehyde Catal Commun 8 1995 1998 10.1016/j.catcom.2007.03.025
37. Heck RF (1985) Palladium reagents in organic synthesis. Academic Press, London
38. Y Nakamura S Takeuchi S Zhang K Okumura Y Ohgo 2002 Preparation of a fluorous chiral BINAP and application to an asymmetric Heck reaction Tetrahedron Lett 43 3053 3056 10.1016/S0040-4039(02)00407-0
39. Y Nakamura S Takeuchi Y Ohgo 2003 Enantioselective carbon-carbon bond forming reactions using fluorous chiral catalysts J Fluor Chem 120 121 129 10.1016/S0022-1139(02)00320-2
40. J Moineau G Pozzi S Quici D Sinou 1999 Palladium-catalyzed heck reaction in perfluorinated solvents Tetrahedron Lett 40 7683 7686 10.1016/S0040-4039(99) 01590-7
41. R Grigg M York 2000 Bimetallic catalytic cascade ring closing metathesis-intra-molecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst Tetrahedron Lett 41 7255 7258 10.1016/S0040-4039(00)01250-8
42. C Rocaboy JA Gladysz 2002 Highly active thermomorphic fluorous palladacycle catalyst precursors for the Heck reaction; evidence for a palladium nanoparticle pathway Org Lett 4 1993 1996 10.1021/ol025790r
43. C Rocaboy JA Gladysz 2003 Thermomorphic fluorous imine and thioether palladacycles as precursors for highly active Heck and Suzuki catalysts; evidence for palladium nanoparticle pathways N J Chem 27 39 49 10.1039/b208545n
44. M Moreno-Mañas R Pleixats S Villarroya 2001 Fluorous phase soluble palladium nanoparticles as recoverable catalysts for Suzuki cross-coupling and Heck reactions Organometallics 20 4524 4528 10.1021/om010442z
45. M Moreno-Mañas R Pleixats S Villarroya 2002 Palladium nanoparticles stabilised by polyfluorinated chains J Chem Soc Chem Commun 1 60 61
46. T Fukuyama M Arai H Matsubara I Ryu 2004 Mizoroki-Heck arylation of α, β-unsaturated acids with a hybrid fluorous ether, F-626: facile filtrative separation of products and efficient recycling of a reaction medium containing a catalyst J Org Chem 69 8105 8107 10.1021/jo049028+
47. DP Curran K Fischer G Moura-Letts 2004 A soluble fluorous palladium complex that promotes heck reactions and can be recovered and reused Synlett 8 1379 1382 10.1055/s-2004-829094
48. WB Yi C Cai X Wang 2007 A novel fluorous Palladium catalyst for Heck reaction in a fluorous biphase system (FBS) J Mol Catal A Chem 274 68 71 10.1016/j.molcata.2007.03.052
49. Herz W, Falk H, Kirby GW, Moore RE (2001) Progress in the chemistry of organic natural products. Springer, New York
50. N Miyara A Suzuki 1995 Palladium-catalyzed cross-coupling reactions of silanolates: a paradigm shift in silicon-based cross-coupling reactions Chem Rev 95 2457 2483 (and reference cited therein)
51. NTS Phan M VanDer Sluys CW Jones 2006 Heck reaction in ionic liquids and the in situ identification of N-heterocyclic carbene complexes of palladium Adv Synth Catal 348 609 679 10.1002/adsc.200505473
52. Schneider S, Bannwarth W (2001) A general route to pyridine-modified salicylaldehydes via Suzuki coupling. Helv Chim Acta 84:735-742. doi:10.1002/1522-2675(20010321)84:3<735::AID-HLCA735>3.0.CO;2-L
53. C Rocaboy JA Gladysz 2002 Syntheses, oxidations, and palladium complexes of fluorous dialkyl sulfides: new precursors to highly active catalysts for the Suzuki coupling Tetrahedron 58 4007 4014 10.1016/S0040-4020(02)00275-2
54. MG Shen C Cai WB Yi 2007 A novel fluorous palladium catalyst for Suzuki reaction in fluorous media J Fluor Chem 127 1421 1424 10.1016/j.jfluchem.2007. 07.008
55. K Sonogashira Y Tohda NA Hagihara 1975 Convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromalkenes, iodoarenes, and bromophyridines Tetrahedron Lett 16 4467 4470 10.1016/S0040-4039(00)91094-3
56. R Chinchilla C Nájera 2007 The Sonogashira reaction: a booming methodology in synthetic organic chemistry Chem Rev 107 874 922 (and reference cited therein)
57. E Negishi L Anastasia 2003 Palladium-catalyzed alkynylation Chem Rev 103 1979 2017 10.1021/cr020377i
58. Li JJ, Gribble GW (2000) Palladium in heterocyclic chemistry. In: Tetrahedron organic chemistry series, vol 20. Pergamon, Amsterdam
59. KC Nicolaou WM Dai 1991 Chemistry and biology of enediyneantieancer antibiotics Angew Chem Int Ed Engl 30 1387 1416 10.1002/anie.199113873
60. JM Grissom GU Gunawardena D Klingberg D Huang 1996 The chemistry of enediynes, enyne allenes and related compounds Tetrahedron 52 6453 6518 10.1016/0040-4020(96)00016-6
61. M De Kort V Correa ARPM Valentijin GA Van der Marel BVL Potter CW Taylor JH Van Boom 2000 Synthesis of potent agonists of the D-myo-inositol 1,4,5-trisphosphate receptor based on clustered disaceharide polyphosphate analogues of adenophostin J Med Chem 43 3295 3303 10.1021/jm000957c
62. V Francke T Mangel K Muellen 1998 Synthesis of α,ω- difunctionalized oligo- and poly(p-phenyleneethynylene)s Macromolecules 31 2447 2453 10.1021/ma971429m
63. Sonogashira K (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 3. Pergamon, New York, 521 pp
64. T Fukuyama M Shinmen S Nishitani M Sato I Ryu 2002 A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling Org Lett 4 1691 1694 10.1021/ol0257732
65. JP Genet E Blart M Savignac 1992 Palladium-catalyzed cross-coupling reactions in a homogeneous aqueous medium Synlett 9 715 717 10.1055/s-1992-21465
66. JZ Jiang C Cai 2006 Pd/C catalyzed Sonogashira coupling reaction of phenylacetylene in TX10 microemulsion Colloids Surf A Physicochem Eng Asp 287 212 216 10.1016/j.colsurfa.2006.03.037
67. KR Reddy NS Kumar PS Reddy B Sreedhar ML Kantam 2006 Cellulose supported palladium(0) catalyst for Heck and Sonogashira coupling reactions J Mol Catal A: Chem 252 12 16 (and reference cited therein)
68. A Corma H Garciá A Primo 2006 Palladium and copper supported on mixed oxides derived from hydrotalcite as reusable solid catalysts for the sonogashira coupling J Catal 241 123 131 10.1016/j.jcat.2006.04.021
69. HF Chow CW Wan KH Low YY Yeung 2001 A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions J Org Chem 66 1910 1913 10.1021/jo001538q
70. L Djakovitch P Rollet 2004 Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites Adv Synth Catal 346 1782 1792 (and reference cited therein)
71. C Yi R Hua 2006 A copper-free efficient palladium(II)-catalyzed coupling of aryl bromides with terminal alkynes Catal Commun 7 377 379 (and reference cited therein)
72. A Cwik Z Hell F Figueras 2006 A copper-free Sonogashira reaction using a Pd/MgLa mixed oxide Tetrahedron Lett 47 3023 3026 (and reference cited therein)
73. NA Powell SD Rychnosky 1996 Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: synthesis of enediynes Tetrahedron Lett 37 7901 7904 10.1016/0040-4039(96)01698-X
74. GT Crisp PD Turner KA Stephens 1998 Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc J Organomet Chem 570 219 224 10.1016/S0022-328X(98)00765-7
75. K Nakamura H Ohubo M Yamaguchi 1999 Low temperature Sonogashira coupling reaction Synlett 5 549 550 10.1055/s-1999-2684
76. GW Kabalka L Wang V Namboodiri RM Pagni 2000 Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina Tetrahedron Lett 41 5151 5154 10.1016/S0040-4039(00)00774-7
77. A Garcia-Bernabé CC Tzschucke W Bannwarth R Haag 2005 Supramolecular immobilization of a perfluoro-tagged Pd-catalyst with dendritic architectures and application in Suzuki reactions Adv Synth Catal 347 1389 1394 (and reference cited therein)
78. WB Yi C Cai X Wang 2007 A novel palladium/perfluoroalkylated-pyridine catalyst for Sonogashira reaction of aryl bromides and chlorides in a fluorous biphasic system (FBS) Eur J Org Chem 11 3445 3448 10.1002/ejoc.200700287
79. 3]: a novel catalyst for the hetero Diels-Alder reaction of aldehydes with non-activated dienes Bull Chem Soc Jpn 70 1421 1426 10.1246/bcsj.70.1421
80. HB Kagan O Riant 1992 Catalytic asymmetric Diels-Alder reactions Chem Rev 92 1007 1019 10.1021/cr00013a013
81. RR Schmidt 1986 Hetero-Diels-Alder reaction in highly functionalized natural product synthesis Acc Chem Res 19 250 259 10.1021/ar00128a004
82. Y Liu E Lotero JG Goodwin Jr 2006 Effect of water on sulfuric acid catalyzed esterification J Mol Catal Chem 245 132 140 10.1016/j.molcata.2005.09. 049
83. MR Altiokka A Citak 2003 Kinetics study of esterification of acetic acid with isobutanol in the presence of amberlite catalyst Appl Catal Gen 239 141 148 10.1016/S0926-860X(02)00381-2
84. GD Yadav PH Mehta 1994 Heterogeneous catalysis in esterification reactions: preparation of phenethyl acetate and cyclohexyl acetate Ind Eng Chem Res 33 2198 2208 10.1021/ie00033a025
85. WB Yi C Cai 2005 Esterification of fluorous biphasic system catalyzed by rare earth(III) perfluorooctanesulfonate Chin J Org Chem 25 1434 1436 (in Chinese)
86. Greene TW, Wats PGM (1999) Protective groups in organic synthesis. Wiley, New York
87. WB Yi YQ Yin C Cai 2006 Ytterbium perfluorooctanesulfonate catalyzed synthesis of acylals from aldehydes and acetic anhydride in a fluorous biphasic system Can J Chem 84 1563 1566 10.1139/V06-162
88. Reeves RL (1966) Chemistry of carbonyl group. Wiley Intersciences, New York
89. WB Yi C Cai 2006 Synthesis of acetals catalyzed by rare earth (III) perfluorooctane sulfonates in fluorous solvent Chin J Appl Chem 23 1295 1297 (in Chinese)
90. Arend M, Westermann B, Risch N (1998) Modern variants of the Mannich reaction. Angew Chem Int Ed 37:1044-1070 (and references cited therein). doi:10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E
91. H Ishitani M Ueno S Kobayashi 1997 Aldehydes vs aldimines. Unprecedented aldimine-selective nucleophilic additions in the coexistence of aldehydes using a lanthanide salt as a Lewis acid catalyst J Am Chem Soc 119 10049 10053 10.1021/ja970498d (and references cited therein)
92. K Manabe S Kobayashi 1999 Mannich-type reactions of aldehydes, amines, and ketones in a colloidal disoersion system created by a Brølnsted acid-surfactant-combined catalyst in water Org Lett 1 1965 1967 10.1021/ol991113u
93. S Limura D Nobutou K Manabe S Kobayashi 2003 Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst Chem Commun 14 1644 1645
94. LM Wang JW Han J Sheng ZY Fan H Tian 2005 Aromatic aldehydes and aromatic amines: three component one-pot synthesis of β-amino ketone derivatives Chin J Org Chem 25 591 594 (in Chinese)
95. WB Yi C Cai 2006 Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media J Fluor Chem 127 1515 1521 10.1016/j.jfluchem.2006.07.009
96. Landquist JK (1984) In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 1. Pergamon, Oxford, pp 166-170
97. R Ricaurte I Braulio A Rodrigo O Jairo 2004 Preparation of some light-sensitive 2-nitrophenyl-2, 3-dihydro-1H-benzodiazepines Arkivoc 13 67 71
98. RC Farges SR Torres F Pascual RM Ribeiro-do-Valle 2004 Involvement of steroids in anti-inflammatory effects of peripheral benzodiazepine receptor ligands Life Sci 74 1387 1395 10.1016/j.lfs.2003.08.013
99. L Kosychova Z Stumbreviciute L Pleckaitiene R Janciene BD Puodziunaite 2004 Synthesis of substituted 5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5] benzodiazepines Chem Heterocycl Compd 40 811 815 10.1023/B:COHC.0000040781. 41929.9c
100. A Chimirri S Grasso R Ottana G Romeo MJ Zappala 1990 Synthesis of substituted 5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines Heterocycl Chem 27 371 375
101. P Stahlofen W Ried 1957 Heterocyclic seven-membered ring systems (V) reaction of o-phenylenediamine with a,b-unsaturated carbonyl compounds Chem Ber 90 815 824 10.1002/cber.19570900528
102. W Ried E Torinus 1959 Heterocyclic seven-ring systems: synthesis of condensed 5-,7- and 8-membered heterocycles with 2 nitrogen atoms Chem Ber 92 2902 2916 10.1002/cber.19590921138
103. R Gheorghe E Comanita C Bogdan 2002 Synthesis and reactivity of Mannich bases. XIV. Base-catalyzed cyclocondensation of β-aminoketones to 1,5-benzodiazepines and 1,4-naphthodiazepines Acta Chim Slov 49 575 585
104. JT Wu F Xu ZQ Zhou Q Shen 2006 Efficient synthesis of 1,5-benzodiazepine derivatives by ytterbium trichloride-catalyzed condensation of o-phenylenediamine and ketones Synth Commun 36 457 464 10.1080/00397910500383527
105. M Curini F Epifano MC Marcotullio O Rosati 2001 Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives Tetrahedron Lett 42 3193 3195 10.1016/S0040-4039(01)00413-0
106. WB Yi C Cai 2007 Ytterbium perfluorooctanesulfonates catalyzed the synthesis of 1,5-benzodiazepine derivatives in fluorous solvents Synth Commun 37 3827 3833 10.1080/00397910701572464
107. JG Lombardino EH Wiseman 1974 Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles J Med Chem 17 1182 1188 10.1021/jm00257a011
108. LM Wang YH Wang T He YF Yao JH Shao B Liu 2006 Ytterbium triflate as an efficient catalyst for one-pot synthesis of substituted imidazoles through three-component condensation of benzil, aldehydes and ammonium acetate J Fluor Chem 127 1570 1537 10.1016/j.jfluchem.2006.08.005
109. MG Shen C Cai WB Yi 2008 Ytterbium perfluorooctanesulfonate as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles J Fluor Chem 129 541 544 10.1016/j.jfluchem.2008.03.009
110. T Roth ML Morningstar PL Boyer SHJ Hughes RW Buckheit CJ Michejda 1997 Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Aryl-substituted benzimidazoles J Med Chem 40 4199 4207 10.1021/jm970096g
111. RW Middleton DG Wibberley 1980 Synthesis of imidazo[4,5 b]- and [4,5 c]pyridines J Heterocycl Chem 17 1757 1760
112. TA Fairley RR Tidwell I Donkor NA Naiman KA Ohemeng RJ Lombardy JA Bentley M Cory 1993 DNA minor groove binding, and base pair specificity of alkyl-and aryl-linked bis(amidinobenzimidazole) and bis(amidinoindoles) J Med Chem 36 1746 1753 10.1021/jm00064a008
113. K Bourgrin A Loupy M Soufiaoui 1998 Three new routes for synthesis 1,3-azolederivatives using microwave Tetrahedron 54 8055 8064 10.1016/S0040-4020(98)00431-1
114. MG Shen C Cai 2007 Ytterbium perfluorooctanesulfonates catalyzed synthesis of benzimidazole derivatives in fluorous solvents J Fluor Chem 128 232 235 10.1016/j.jfluchem.2007.01.009
115. Ingold CK (1969) Structure and mechanism in organic chemistry, 2nd ed. Cornell University Press, Ithaca
116. Olah GA, Malhotra R, Narang SC (1989) Nitration: methods and mechanism. VCH Publishers, New York
117. Schofield K (1980) Aromatic nitration. Cambridge University Press, London
118. LV Malysheva EA Paukshtis KG Ione 1995 Nitration of aromatics by nitrogen oxides on zeolite catalysts: comparison of reaction in the gas phase and solutions Catal Rev Sci Eng 37 179 226
119. FJ Waller AGM Barrett DC Braddock RM McKinnell AJP White DJ Williams R Ducray 1999 Tris(trifluoromethanesulfonyl)methide ("triflide") anion: convenient preparation, X-ray crystal structures, and exceptional catalytic activity as a counterion with Ytterbium(III) and Scandium(III) J Org Chem 64 2910 2913 10.1021/jo9800917 (and references cited therein)
120. M Shi SC Cui 2002 Electrophilic aromatic nitration using perfluorinated rare earth metal salts in fluorous phase Chem Commun 9 994 995 10.1039/b202308n
121. MR Crampton EL Cropper LM Gibbons RW Millar 2002 The nitration of arenes in perfluorocarbon solvents Green Chem 4 275 278 10.1039/b200627h
122. WB Yi C Cai 2006 Highly efficient dinitration of aromatic compounds in fluorous media using Ytterbium perfluorooctanesulfonate and perfluorooctanesulfonic acid as catalysts Synth Commun 36 2957 2961 10.1080/00397910600773700
123. CL Coon WG Blucher ME Hill 1973 Aromatic nitration with nitric acid and trifluoromethanesulfonic acid J Org Chem 38 4243 4248 10.1021/jo00964a007
124. S Kobayashi M Sugiura MH Kitagawa WL Lam 2002 Rare-earth metal triflates in organic synthesis Chem Rev 102 2227 2302 10.1021/cr010289i (and references cited therein)
125. AJ Hill RW Millar JPB Sandall 2004 Atom-efficient eletrophilic aromatic nitration by dinitrogen pentoxide catalysed by zirconium(IV) 2,4-pentanedionate Org Biomol Chem 1 90 92 10.1039/b311068k (and references cited therein)
126. XH Peng H Suzuki 2001 Regioselective double Kyodai nitration of toluene and chlorobenzene over zeolites High preference for the 2,4-dinitro isomer at the second nitration stage Org Lett 3 3431 3434 10.1021/ol016283x (and references cited therein)
127. WB Yi C Cai 2007 A novel and highly efficient catalytic system for trinitration of aromtatic compounds: Ytterbium perfluorooctanesulfonate and perfluorooctanesulfonic acid in fluorous solvents J Energ Mater 25 129 139 10.1080/07370650701205790
128. GA Olah HCH Lin 1971 Electrophilic reactions at single bonds, V. Nitration and nitrolysis of alkanes and cycloalkanes with nitronium salts J Am Chem Soc 93 1259 1261 10.1021/ja00734a039
129. WE Bachmann WJ Horton EL Jenner NW MacNaughton LB Scott 1951 Cyclic and linear nitramines formed by nitrolysis of hexamine J Am Chem Soc 73 2769 2773 10.1021/ja01150a099
130. JH Robson J Reinhart 1955 The synthesis of secondary nitramines by the nitrolysis of N,N-disubstituted amides J Am Chem Soc 77 2453 2457 10.1021/ja01614a028
131. LW Perkins KT Klasson RM Counce PR Bienkowski 2003 Development of nitrolysis for excess sludge treatment II: a factorial study for industrial wastes Ind Eng Chem Res 42 5457 5461 10.1021/ie0304311
132. LW Perkins KT Klasson RM Counce PR Bienkowski 2003 Development of nitrolysis for excess sludge treatment: a factorial study Ind Eng Chem Res 42 3544 3548 10.1021/ie030125n
133. Olah G, Squire ADR (1991) Chemistry of energetic materials. Academic Press Inc., San Diego
134. Millar RW, Colclough ME, Desai H (1996) Novel syntheses of energetic materials. British Crown, UK
135. GC Hale 1925 Nitration of urotropine using nitric acid J Am Chem Soc 47 2754 2757 10.1021/ja01688a017
136. WJ Dunning B Millard CW Nutt 1952 The heat of nitrolysis of hexamine in nitric acid J Chem Soc 9 1264 1269 10.1039/jr9520001264
137. BWE Bachmann JC Sheehan 1949 A new method of preparing the high explosive RDX J Am Chem Soc 71 1842 1845 10.1021/ja01173a092
138. WB Yi C Cai 2008 Synthesis of RDX by nitrolysis of hexamethylenetetramine in fluorous media J Hazard Mater 150 839 842 10.1016/j.jhazmat.2007.10.040
139. Succasunna WL, Saddlebrook SN, Alster J, Lawn F (1992) Improved process of producing HMX in 100% yield and purity. US 5124493.
140. Siele VI (1976) Process for producing 1,3,5,7-tetraalkanoyl-1,3,5,7- octahydrotetrazocines. US 3979379
141. McGuire RR, Coon CL, Richard K (1984) Method for synthesizing HMX. US 4432902.
142. YF Y CJ Huang 1989 Study on preparation of HMX by DANNO method Chin J Explos Pyrot 12 1 4 (in Chinese)
143. TS Ren H Yan 1991 Studies on HMX synthesis from paraformaldehyde and ammonium nitrate Proc Int Pyrotech Semin 1 220
144. Coon CJ (1976) Preparation of octahydro-1,3,5,7-tetraalkanoyl-1,3,5,7- tetrazocines. US 3978046
145. Larock RC (1989) Comprehensive organic transformations. VCH Publishers Inc., New York
146. BP Buffin JP Clarkson NL Belitz A Kundu 2005 Pd(II)-biquinoline catalyzed aerobic oxidation of alcohols in water J Mol Catal Chem 225 111 116 10.1016/j.molcata.2004.08.035 (and references cited therein)
147. Yi WB, Cai C (2007) New method for preparation of benzaldehyde from benzyl alcohol in fluorous biphasic system. CN 1927798 (in Chinese)
148. B Betzemeier M Cavazzini S Quici P Knochel 2000 Copper-catalyzed aerobic oxidation of alcohols under fluorous biphasic conditions Tetrahedron Lett 41 4343 4346 10.1016/S0040-4039(00)00620-1
149. T Nishimura Y Maeda N Kakiuchi S Uemura 2000 Palladium(II)-catalysed oxidation of alcohols under an oxygen atmosphere in a fluorous biphase system (FBS) J Chem Soc Perkin Trans I 24 4301 4305 10.1039/b006874h
150. f-bipyridine complexes - their catalytic activity in the oxidation of hydrocarbons, olefins, and alcohols, including mechanistic implications Chem Eur J 9 4168 4178 10.1002/chem.200304771
151. Vincent JM, Lastécouères D, Contel M, Laguna M, Fish RH (2004) In: Gladysz JA, Curran DP, Horváth IT (eds) Handbook of fluorous chemistry, chaps 10,12. Willey, New York, pp 298-305
152. Vincent JM, Contel M, Laguna M, Fish RH (2004) In: Gladysz JA, Curran DP, Horváth IT (eds) Handbook of fluorous chemistry, chaps 11,15. Willey, New York, pp 395-397
153. 3+, embedded in surface-derivatized silica, as an MMO model and fluorous biphasics catalysis for alkane, alkene and alcohol oxidation chemistry Top Catal 32 185 196 10.1007/s11244-005-2890-9
154. M Contel PR Villuendas J Fernandez-Gauardo PJ Alonso JM Vincent RH Fish 2005 Fluorocarbon soluble copper(II) carboxylate complexes with nonfluoroponytailed nitrogen ligands as precatalysts for the oxidation of alkenols and alcohols under fluorous biphasic or thermomorphic modes: structural and mechanistic aspects Inorg Chem 44 9771 9778 10.1021/ic051220m
155. WB Yi C Cai 2006 Cobalt(II) perfluorooctane sulfonate catalyzed highly efficient aerobic oxidation of alcohols in fluorous biphasic systems Aust J Chem 59 349 353 10.1071/CH05250
156. O Miersch R Kramell B Parthier C Wasternack 1999 Structure-activity relations of substituted, deleted or stereospecifically altered jasmonic acid in gene expression of barley leaves Phytochemistry 50 353 361 10.1016/S0031- 9422(98)00597-4
157. JRE Hoover GL Dunn DR Jakas LL Lam JJ Taggart JR Guarini L Phillips 1974 Semisynthetic cephalosporins. Synthesis and structure-activity relationships of 7-mandelamido-3-cephem-4-carboxylic acids J Med Chem 17 34 41 10.1021/jm00247a008
158. M Yoshioka A Yoshida Y Ichihashi H Saito 1985 Homovanillic acid, vanillylmandelic acid and 5-hydroxyindole-3-acetic acid are undetectable in urine of the muskrat Chem Pharm Bull 33 2145 2148
159. AE El Nimr HA Salama RM Khalil MA Kassem 1983 Effects of urea on the activity of certain ophthalmic drugs in man Pharmazie 38 728 730
160. Corson BB (1941). In: Orgnanic synthesis, vol I. Wiley, New York, 336 pp
161. A Merz 1974 Phase transfer-catalyzed reactions IV Simple mandelic acid synthesis. Synthesis 10 724 725 10.1055/s-1974-23421
162. Aston JG (1955). In: Orgnanic synthesis, vol III. Wiley, New York, 538 pp
163. C Massimo E Francesco G Salvatore M Carla Marcotullio R Ornelio 2005 Ytterbium triflate-promoted tandem one-pot oxidation-Cannizzaro reaction of aryl methyl ketones Org Lett 7 1331 1333 10.1021/ol050125e
164. MG Shen C Cai 2007 Rare earth (III) perfluorooctanesulfonates catalyzed synthesis of α-hydroxy-arylacetic acids from aryl methyl ketones in fluorous media Catal Commun 8 871 875 10.1016/j.catcom.2006.08.045
165. IA Koppel RW Taft F Anvia SZ Zhu LQ Hu KS Sung DD DesMarteau LM Yagupolskii YL Yagupolskii NV Ignat'ev NV Kondratenko AY Volkonskii VM Vlasov R Notario PC Maria 1994 The gas-phaseacidities of very strong neutral brønsted acids J Am Chem Soc 116 3047 3057 10.1021/ja00086a038
166. XH Hao A Yoshida J Nishikido 2006 Metal bis(perfluorooctanesulfonyl) amides as highly efficient Lewis acid catalysts for fluorous biphase organic reactions J Fluor Chem 127 193 199 10.1016/j.jfluchem.2005.10.017
167. J Nishikido A Yoshida 2005 Development of multiphase reaction processes using fluorous Lewis acid catalysts J Synth Org Chem, Jpn 63 144 153
168. K Mikami Y Mikami H Matsuzawa J Nishikido F Yamamoto H Nakajima 2002 Lanthanide catalysts with tris(perfluorooctane-sulfonyl)methide and bis(perfluorooctanesulfonyl) amide ponytails: recyclable Lewis acid catalysts in fluorous phases or as solids Tetrahedron 58 4015 4021 10.1016/S0040-4020(02) 00313-7
169. 4-Catalyzed Friedel-Crafts acylation in a fluorous biphase system Tetrahedron Lett 46 2697 2700 10.1016/j.tetlet.2005.02. 065
170. E Arundale LA Mikeska 1952 The olefin-aldehyde condensation The Prins reaction. Chem Rev 51 505 556 10.1021/cr60160a004
171. Zhang WC, Viswanathan GS, Li CJ (1999) Scandium triflate catalyzed in situ Prins-type cyclization: formations of 4-tetrahydropyranols and ethers. Chem Commun 291-292. doi: 10.1039/a808960d
172. WC Zhang CJ Li 2000 Diastereoselective synthesis of 2, 4-disubstituted tetrahydropyranols and ethers via Prins-type cyclization catalyzed by scandium triflate Tetrahedron 56 2403 2411 10.1016/S0040-4020(00)00152-6
173. XH Hao A Yoshida N Hoshi 2007 Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel-Crafts acylation and Prins reaction in fluorous biphase system J Fluor Chem 128 1396 1401 10.1016/j.jfluchem.2007.07.007
174. XQ Yao CJ Li 2004 Highly efficient addition of activated methylene compounds to alkenes catalyzed by gold and silver J Am Chem Soc 126 6884 6885 (and reference cited therein)
175. M Reping BJ Nachtsheim W Ieawsuwan 2006 An effective bismuth-catalyzed benzylation of arenes and heteroarenes Adv Synth Catal 348 1033 1037 (and reference cited therein)
176. M Reping BJ Nachtsheim A Kuenkel 2007 Efficient metal-catalyzed direct benzylation and allylic alkylation of 2,4-pentanediones Org Lett 9 825 828 (and reference cited therein)
177. Tsuji J (2000) Palladium reagents and catalysts, innovations in organic synthesis 2nd ed. Wiley, Chichester
178. 3 catalyzed alkylation of 1,3-dicarbonyl compounds using alcohols as substrates Tetrahedron Lett 48 3969 3973 10.1016/j.tetlet.2007.04.047
179. JP Poupelin G Sanit-Ruf O Foussard-Blanpin G Marcisse G Uchida-Ernouf R Lacroix 1978 Synthesis and antiinflammatory properties of bis(2 hydroxy 1 naphthyl) methane derivatives Eur J Med Chem 13 67 71
180. RM Ion D Frackowiak A Planner K Wiktorowicz 1998 The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy Acta Biochim Pol 45 833 845
181. RJ Sarma JB Baruah 2005 One step synthesis of dibenzoxanthenes Dyes Pigm 64 91 92 10.1016/j.dyepig.2004.03.010
182. M Ahmad TA King DK Ko BH Cha J Lee 2002 Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases J Phys D Appl Phys 35 1473 1476 10.1088/0022-3727/35/13/303
183. JX Liu ZJ Diwu WY Leung 2001 Synthesis and photophysical properties of new fluorinated benzo[c]xanthene dyes as intracellular pH indicators Bioorg Med Chem Lett 11 2903 2905 10.1016/S0960-894X(01)00595-9
184. AI Oliva L Simón FM Muñiz F Sanzb JR Morán 2004 A trans-tetrahydrobenzoxanthene receptor for the resolution of racemic mixtures of sulfonylamino acids Chem Commun 4 426 427 10.1039/b312560b
185. 3 as an efficient catalyst under solvent-free conditions Chin J Chem 26 1105 1108 10.1002/cjoc.200890196
186. XH Hao A Yoshida J Nishikido 2004 Recyclable and selective Lewis acid catalysts for transesterification and direct esterification in a fluorous biphase system: tin(IV) and hafnium(IV) bis(perfluorooctanesulfonyl)amide complexes Tetrahedron Lett 45 781 785 10.1016/j.tetlet.2003.11.035
187. K Ishihara M Nakayama S Ohara H Yamamoto 2002 Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts Tetrahedron 58 8179 8188 10.1016/S0040-4020(02)00966-3
188. J Otera 1993 Transesterification Chem Rev 93 1449 1470 10.1021/cr00020a004
189. Renz M, Meunier B (1999) 100 Years of Baeyer-Villiger Oxidations. Eur J Org Chem 4:737-750. doi:10.1002/(SICI)1099-0690(199904)1999:4<737::AID- EJOC737>3.0.CO;2-B
190. XH Hao O Yamazaki A Yoshida J Nishikido 2003 Tin(IV) bis(perfluoroalkanesulfonyl)amide complex as a highly selective Lewis acid catalyst for Baeyer-Villiger oxidation using hydrogen peroxide in a fluorous recyclable phase Tetrahedron Lett 44 4977 4980 10.1016/S0040-4039(03)01185-7
191. G Pozzi S Quici RH Fish 2008 Fluorous phase transfer catalyst: from onium salts to crown ethers J Fluor Chem 129 920 929 10.1016/j.jfluchem.2008.06.001
192. Qiu W (2000) Fluorinated quaternary ammonium salts. US 6054615
193. G Maayan RH Fish R Neumann 2003 Polyfluorinated quaternary ammonium salts of polyoxometalate anions: fluorous biphasic oxidation catalysis with and without fluorous solvents Org Lett 5 3547 3550 10.1021/ol0348598
194. L Mercs G Pozzi S Quici 2007 Efficient condensation of carboxylic acids with alcohols catalyzed by fluorous ammonium triflates Tetrahedron Lett 48 3053 3056 10.1016/j.tetlet.2007.02.117
195. S Shirakawa Y Tanaka K Maruoka 2004 Development of a recyclable fluorous chiral phase-transfer catalyst: application to the catalytic asymmetric synthesis of α-amino acids Org Lett 6 1429 1431 10.1021/ol049724w
196. W Shen LM Wang H Tian 2008 The synthesis of organoantimony(III) difluorides containing Y,C,Y pincer type ligands using organotin(IV) fluorinating agents J Fluor Chem 129 267 273 10.1016/j.jfluchem.2007.12.002
197. C Emnet KM Weber JA Vidal CS Consorti AM Stuart JA Gladysz 2006 Syntheses and properties of fluorous quaternary phosphonium salts that bear four ponytails; new candidates for phase transfer catalysts and ionic liquids Adv Synth Catal 348 1625 1634 10.1002/adsc.200606138
198. CS Consorti M Jurisch JA Gladysz 2007 Ionic transformations in extremely nonpolar fluorous media: phase transfer catalysis of halide substitution reactions Org Lett 9 2309 2312 10.1021/ol0706354
199. 2 conditions Green Chem 5 92 94 10.1039/b210007j
200. G Vlád FU Richter IT Horváth 2004 Modular synthesis of fluorous trialkylphosphines Org Lett 6 4559 4561 10.1021/ol0480675
201. 3 Tetrahedron Lett 46 8605 8608 10.1016/j.tetlet.2005.09.166
202. Montanari F, Quici S, Banfi S (1996) Phase-transfer catalysis. In: Reinhoudt DN (ed) Comprehensive supramolecular chemistry, vol 10. Pergamon, Oxford, pp 389-416
203. WH Lin WI Bailey RJ Lagow 1985 The first perfluoro crown ethers J Chem Soc Chem Commun 9 1350 1352 10.1039/c39850001350
204. TY Lin WH Lin WD Clark RJ Lagow SB Larson SH Simonsen VM Lynch JS Brodbelt SD Maleknia CC Liou 1994 Synthesis and chemistry of perfluoro macrocycles J Am Chem Soc 116 5172 5179 10.1021/ja00091a022 (and references therein)
205. J Chen YF Zhang X Zheng A Vij D Wingate D Meng K White RL Kirchmeier JM Shreeve 1996 Synthesis of cyclic ethers with fluorinated side chains Inorg Chem 35 1590 1601 10.1021/ic9509645
206. 2 Angew Chem Int Ed Engl 36 2346 2349 10.1002/anie.199723461
207. G Pozzi M Cavazzini S Quici S Fontana 1997 Metal complexes of a tetraazacyclotetradecane bearing highly fluorinated tails: new catalysts for the oxidation of hydrocarbons under fluorous biphasic conditions Tetrahedron Lett 38 7605 7608 10.1016/S0040-4039(97)01805-4
208. S Elshani E Kobzar RA Bartsch 2000 Macrocyclic ligands with partially fluorinated sidearms: synthesis and metal ion complexation Tetrahedron 56 3291 3301 10.1016/S0040-4020(00)00248-9
209. AM Stuart JA Vidal 2007 Perfluoroalkylated 4,13-diaza-18-crown-6 ethers: synthesis, phase-transfer catalysis, and recycling studies J Org Chem 72 3735 3740
210. Pozzi G, Quici S, Fish RH (2007) In: Proceedings of the 2nd international symposium on fluorous technologies (ISoFT'07), Yokohama, Paper O1