On the reactivity and stability of electrogenerated N-heterocyclic carbene in parent 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate: Formation and use of N-heterocyclic carbene-CO2 adduct as latent catalyst

Electrochimica Acta

Volumn 109, Issue , 2013, Pages 95-101

  Feroci, Marta ^a   Chiarotto, Isabella ^a   Vecchio Ciprioti, Stefano ^a   Inesi, Achille ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b NONE   (Italy)

Author keywords

Carbon dioxide; Cathodic reduction; N heterocyclic carbene

Indexed keywords

CARBON; CATALYSTS; IONIC LIQUIDS; ORGANIC COMPOUNDS;

BENZOIN CONDENSATION; CATHODIC REDUCTIONS; GALVANOSTATIC CONDITIONS; LATENT CATALYSTS; N-HETEROCYCLIC CARBENES; OXIDATIVE ESTERIFICATIONS; ROOM TEMPERATURE IONIC LIQUIDS; TETRAFLUOROBORATES;

CARBON DIOXIDE;

EID: 84880982979     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.07.115     Document Type: Article

References (51)

1. B.C. Norris, D.G. Sheppard, G. Henkelman, C.W. Bielawski, Kinetic and thermo-Dynamic evaluation of the reversible N-Heterocyclic carbene- Isothiocyanatecoupling reaction: Applications in latent catalysis, Journal of Organic Chemistry76 2011 301, and references therein.
2. R.T.M. Jakobs, R.P. Sijbesma, Mechanical activation of a latent olefin metathe-Sis catalyst and persistence of its active species in ROMP, Organometallics 312012 2476, and references therein.
3. H.-W. Wanzlick, E. Schikora, Ein neuer zugang zur carben-Chemie, Angewandte Chemie International Edition 72 1960 494.
4. H.-W. Wanzlick, Aspects of nucleophilic carbene chemistry, Angewandte Chemie International Edition 1 1962 75.
5. H.-W. Wanzlick, H.-J. Schonherr, Direct synthesis of a mercury salt-Carbenecomplex, Angewandte Chemie International Edition 7 1968 141.
6. A.J. Arduengo III, R.L. Harlow, M.K. Kline, A stable crystalline carbene, Journalof the American Chemical Society 113 1991 361.
7. A. Igau, H.G. Grutzmacher, A. Baceiredo, G. Bertrand, Analogous.alpha.,.alpha.?-Bis-Carbenoid, triply bonded species: Synthesis of a stable.lambda.3-Phosphinocarbene-.lambda.5-Phosphaacetylene, Journal of the American Chemical Soci-Ety 110 1988 6463.
8. S. Diez-Gonzalez, N. Marion, S.P. Nolan, N-Heterocyclic carbenes in late transi-Tion metal catalysis, Chemical Reviews 109 2009 3612.
9. F.E. Hahn, M.C. Jahnke, Heterocyclic carbenes: Synthesis and coordinationchemistry, Angewandte Chemie International Edition 47 2008 3122.
10. S. Wurtz, F. Glorius, Surveying sterically demanding N-Heterocyclic carbeneligands with restricted flexibility for palladium-Catalyzed cross-Coupling reac-Tions, Accounts of Chemical Research 41 2008 1523.
11. D. Enders, O. Niemeier, A. Hanseler, Organocatalysis by N-Heterocyclic car-Benes, Chemical Reviews 107 2007 5606.
12. N. Marion, S. Diez-Gonzalez, S.P. Nolan, N-Heterocyclic carbenes as organocat-Alysts, Angewandte Chemie International Edition 46 2007 2988.
13. V. Nair, S. Vellalath, B.P. Babu, Recent advances in carbon-Carbon bond-Formingreactions involving homoenolates generated by NHC catalysis, Chemical Soci-Ety Reviews 37 2008 2691.
14. J.L. Moore, T. Rovis, Lewis base catalysts: Carbene catalysts, Topics in CurrentChemistry 291 2009 77.
15. P.-C. Chiang, J.W. Bode, N-Heterocyclic Carbenes, The Royal Society of Chem-Istry, Cambridge, 2011, pp. 399-435.
16. D.T. Cohen, K.A. Scheidt, Cooperative lewis acid/N-Heterocyclic carbene catal-ysis, Chemical Science 3 2012 53.
17. P.-C. Chiang, J.W. Bode, Asymmetric Organocatalysis, vol. 1, Georg Thieme Ver-Lag, Stuttgart, 2012, pp. 639-672.
18. H.U. Vora, P. Wheeler, T. Rovis, Exploiting acyl and enol azolium intermedi-Ates via N-Heterocyclic carbene-Catalyzed reactions of-Reducible aldehydes,Advanced Synthesis and Catalysis 354 2012 1617.
19. X. Bugaut, F. Glorius, Organocatalytic umpolung: N-Heterocyclic carbenes andbeyond, Chemical Society Reviews 41 2012 3511.
20. A.T. Biju, N. Kuhl, F. Glorius, Extending NHC-Catalysis: Coupling aldehydes withunconventional reaction partners, Accounts of Chemical Research 44 20111182.
21. A. Grossmann, D. Enders, N-Heterocyclic carbene catalyzed domino reactions,Angewandte Chemie International Edition 51 2012 314.
22. V.R. Pattabiraman, J.W. Bode, Rethinking amide bond synthesis, Nature 4802011 471.
23. K. Scheidt, Organic chemistry: Amide bonds made in reverse, Nature 465 20101020.
24. J. Mahatthananchai, J.W. Bode, The effect of the N-Mesityl group in NHC-Catalyzed reactions, Chemical Science 3 2012 192.
25. T. Dröge, F. Glorius, The measure of all rings-N-Heterocyclic carbenes, Ange-wandte Chemie International Edition 49 2010 6940.
26. D. Bourissou, O. Guerret, F.P. Gabbai, G. Bertrand, Stable carbenes, ChemicalReviews 100 2000 39.
27. M.K. Denk, A. Thadani, K. Hatano, A.J. Lough, Sterisch gehinderte stabilenucleophile carben, Angewandte Chemie International Edition 109 19972719.
28. M.K. Denk, A. Thadani, K. Hatano, A.J. Lough, Steric stabilization ofnucleophilic carbenes, Angewandte Chemie International Edition 36 19972607.
29. I. Chiarotto, M. Feroci, G. Sotgiu, A. Inesi, Electrogenerated N-Heterocyclic car-Bene in the parent room temperature ionic liquid as efficient medium for thetransesterification/acylation reaction, European Journal of Organic Chemistry2013 326.
30. M. Feroci, I. Chiarotto, A. Inesi, Internal redox amidation of-Unsaturatedaldehydes in ionic liquids. The electrochemical route, Electrochimica Acta 892013 692.
31. M. Feroci, I. Chiarotto, M. Orsini, R. Pelagalli, A. Inesi, Umpolung reactions inionic liquid catalyzed by electrogenerated N-Heterocyclic carbenes. Synthe-Sis of saturated esters from activated-Unsaturated aldehydes, Chemical Communications 48 2012 5361.
32. M. Orsini, I. Chiarotto, M.M.M. Feeney, M. Feroci, G. Sotgiu, A. Inesi, Umpol-Ung of-Unsaturated aldehydes by electrogenerated NHCs in ionic liquids:synthesis of-Butyrolactones, Electrochemistry Communications 13 2011738.
33. I. Chiarotto, M. Feroci, M. Orsini, M.M.M. Feeney, A. Inesi, Study on the reactivityof aldehydes in electrolyzed ionic liquids. benzoin condensation: VOCs VolatileOrganic Compounds vs RTILs Room Temperature Ionic Liquids, Advanced Synthesis and Catalysis 352 2010 3287.
34. M. Feroci, I. Chiarotto, M. Orsini, A. Inesi, Electrogenerated NHC as an organocat-Alyst in the staudinger reaction, Chemical Communications 46 2010 4121.
35. M. Orsini, I. Chiarotto, G. Sotgiu, A. Inesi, Polarity reversal induced by electro-Chemically generated thiazol-2-ylidenes: The stetter reaction, ElectrochimicaActa 55 2010 3511.
36. M. Orsini, I. Chiarotto, M.N. Elinson, G. Sotgiu, A. Inesi, Benzoin condensa-Tion in 1,3-Dialkylimidazolium ionic liquidsvia electrochemical generation ofN-Heterocyclic carbene, Electrochemistry Communications 11 2009 1013.
37. M. Feroci, M. Orsini, L. Rossi, A. Inesi, Green solvents and precursors of N-Heterocyclic carbenes, Current Organic Synthesis 9 2012 40.
38. B.R. Van Ausdall, J.L. Glass, K.M. Wigging, A.M. Aarif, J. Louie, A systematicinvestigation of factors influencing the decarboxylation of imidazolium car-Boxylates, Journal of Organic Chemistry 74 2009 7935.
39. H.A. Duong, T.N. Tekavec, A.M. Arif, J. Louie, Reversible carboxylation of N-Heterocyclic carbenes, Chemical Communications 2004 112.
40. H. Zhou, W.-Z. Zhang, C.-H. Liu, J.-P. Qu, X.-B. Lu, CO2Adducts of N-Heterocycliccarbenes: Thermal stability and catalytic activity toward the coupling of CO2with epoxides, Journal of Organic Chemistry 73 2008 8039.
41. Y. Kayaki, M. Yamamoto, T. Ikariya, N-Heterocyclic carbenes as efficientorganocatalysts for CO2fixation reactions, Angewandte Chemie InternationalEdition 48 2009 4194.
42. H. Zhou, Y.-M. Wang, W.-Z. Zhang, J.-P. Qu, X.-B. Lu, N-Heterocyclic carbenefunctionalized MCM-41 as an efficient catalyst for chemical fixation of carbondioxide, Green Chemistry 13 2011 644.
43. M.J. Ajitha, C.H. Suresh, NHC catalyzed CO2fixation with epoxides: Probablemechanisms revealter molecular pathway, Tetrahedron Letters 52 2011 5403.
44. M. Fèvre, P. Coupillaud, K. Miqueu, J.-M. Sotiropoulos, J. Vignolle, D. Taton,Imidazolium hydrogen carbonates versus imidazolium carboxylates as organicprecatalysts for N-Heterocyclic carbene catalyzed reactions, Journal of OrganicChemistry 77 2012 10135.
45. L.-X. Wu, H. Wang, Y. Xiao, Z.-Y. Tu, B.-B. Ding, J.-X. Lu, Synthesis of dialkyl car-Bonates from CO2and alcohols via electrogenerated N-Heterocyclic carbenes,Electrochemistry Communications 25 2012 116.
46. V.M. Hultgren, A.W.A. Mariotti, A.M. Bond, A.G. Wedd, Reference poten-Tial calibration and voltammetry at macrodisk electrodes of metallocenederivatives in the ionic liquid Analytical Chemistry 74 20023151.
47. A. Saheb, J. Janata, M. Josowicz, Reference electrode for ionic liquids, Electro-Analysis 18 2006 405.
48. B. Gorodetsky, T. Ramnial, N.R. Branda, J.A.C. Clyburne, Electrochemical reduc-Tion of an imidazolium cation: A convenient preparation of imidazol-2-ylidenesand their observation in an ionic liquid, Chemical Communications 20041972.
49. M. Smiglak, J. Holbrey, S.T. Griffin, W.M. Reichert, R.P. Swatloski, A.R. Katritzky,H. Yang, K. Kirichenko, R.D. Rogers, Ionic liquids via reaction of the zwitterionic1,3-Dimethylimidazolium-2-Carboxylate with protic acids. Overcoming syn-Thetic limitations and establishing new halide free protocols for the formationof ILs, Green Chemistry 9 2007 90.
50. A. Tudose, A. Demonceau, L. Delande, Imidazolinium-2-Carboxylates asN-Heterocyclic carbene precursors in ruthenium-Arene catalysts for olefinmetathesisand cyclopropanation, Journal of Organometallic Chemistry 6912006 5356.
51. M. Feroci, M. Orsini, A. Inesi, An efficient combined electrochemical andultrasound assisted synthesis of imidazole-2-Thiones, Advanced Synthesis andCatalysis 351 2009 2067.