Triethanolammonium acetate as a multifunctional ionic liquid in the palladium-catalyzed green Heck reaction

Journal of Molecular Modeling

Volumn 18, Issue 2, 2012, Pages 433-440

  Petrović, Zorica D ^a   Marković, Svetlana ^a   Petrović, Vladimir P ^a   Simijonović, Dušica ^a  

^a UNIVERSITY OF KRAGUJEVAC   (Serbia)

Author keywords

Green Heck reaction; Pd(0) catalytically active complex; Pd(II) precatalyst; Reaction mechanism; Triethanolamine ionic liquid

Indexed keywords

ACETIC ACID DERIVATIVE; IONIC LIQUID; PALLADIUM; TRIETHANOLAMINE; TRIETHANOLAMMONIUM ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; EXPERIMENTAL STUDY; GREEN HECK REACTION; HECK REACTION; PRIORITY JOURNAL;

CARBOHYDRATE CONFORMATION; CATALYSIS; ETHANOLAMINES; IONIC LIQUIDS; MODELS, MOLECULAR; PALLADIUM;

EID: 84860481495     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1052-1     Document Type: Article

References (35)

1. Heck RF (1979) Palladium-catalyzed reactions with olefins of organic halides. Acc Chem Res 12:146-151
2. Heck FR (1985) Palladium reagents in organic synthesis. Academic, London
3. Heck FR (1991) In: Trost MB, Flemming I (eds) Comprehensive organic synthesis, vol Pergamon, Oxford
4. Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions. Wiley-VCH, New York
5. Carmichael AJ, Earle MJ, Holbrey JD, McCormac PB, Seddon KR (1999) The Heck reaction in ionic liquids: a multiphasic catalyst system. Org Lett 1:997-1000
6. Ye C, Xiao JC, Twamley B, LaLonde AD, Norton MG, Shreeve JM (2007) Basic ionic liquids: facile solvents for carbon-carbon bond formation reactions and ready access to palladium nanoparticles. Eur J Org Chem 5095-5100
7. Wang L, Li H, Li P (2009) Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction. Tetrahedron 65:364-368
8. Xu L, Chen W, Xiao J (2000) Heck reaction in ionic liquids and the in situ identification of N-heterocyclic carbene complexes of palladium. Organometallics 19:1123-1127
9. Pryjomska-Ray I, Trzeciak AM, Ziółkowski JJ (2006) Base-free efficient palladium catalyst of Heck reaction in molten tetrabutylammonium bromide. J Mol Catal A Chem 257:3-8 (Pubitemid 44332302)
10. Henriksen ST, Norrby PO, Kaukoranta P, Andersson PG (2008) Combined experimental and theoretical study of the mechanism and enantioselectivity of palladium-catalyzed intermolecular Heck coupling. J Am Chem Soc 130:10414-10421
11. Surawatanawong P, Hall MB (2008) Theoretical study of alternative pathways for the Heck reaction through dipalladium and "ligand-free" palladium intermediates. Organometallics 27:6222-6232
12. Surawatanawong P, Fan Y, Hall MB (2008) Density functional study of the complete pathway for the Heck reaction with palladium diphosphines. J Organomet Chem 693:1552-1563
13. Petrović ZD, Marković S, Simijonović D, Petrović VP (2009) Mechanistic insight into the preactivation of a modern palladium catalyst precursor in phosphine-free Heck reactions. Monatsh Chem 140:371-374
14. Marković S, Petrović ZD, Petrović VP (2009) DFT study on the preactivation reaction of a palladium catalyst precursor in phosphine-free Heck reactions. Monatsh Chem 140:171-175
15. Goossen LJ, Koley D, Hermann H, Thiel W (2005) Mechanistic pathways for oxidative addition of aryl halides to palladium(0) complexes: a DFT study. Organometallics 24:2398-2410 (Pubitemid 40690747)
16. Green JC, Herbert BJ, Lonsdale R (2005) Oxidative addition of aryl chlorides to palladium N-heterocyclic carbene complexes and their role in catalytic arylamination. J Organomet Chem 690:6054-6067 (Pubitemid 41637969)
17. Cui X, Li Z, Tao ZC, Xu Y, Li J, Liu L, Guo QX (2006) N, Ndimethyl- β-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction. Org Lett 8:2467-2470 (Pubitemid 43980419)
18. Ahlquist M, Norrby PO (2007) Oxidative addition of aryl chlorides to monoligated palladium(0): A DFT-SCRF study. Organometallics 26:550-553
19. Li Z, Fu Y, Guo QX, Liu L (2008) Theoretical study on monoligated Pd-catalyzed cross-coupling reactions of aryl chlorides and bromides. Organometallics 27:4043-4049
20. Huang YL, Weng CM, Hong FE (2008) Density functional studies on palladium-catalyzed Suzuki-Miyaura cross-coupling reactions assisted by N- or P-chelating ligands. Chem Eur J 14:4426-4434
21. Petrović ZD, Petrović VP, Simijonović D, Marković S (2009) Mechanistic pathways for oxidative addition of aryl iodides to the low-ligated diethanolamine palladium(0) complex in phosphine-free Heck reactions. J Organomet Chem 694:3852-3858
22. Deeth RJ, Smith A, Hii KKM, Brown JM (1998) The Heck Olefination reaction; a DFT study of the elimination pathway. Tetrahed Lett 39:3229-3232 (Pubitemid 28197996)
23. Graham DC, Cavell KJ, Yates BF (2006) The influence of Nsubstitution on the reductive elimination behaviour of hydrocarbylpalladium- carbene complexes-a DFT study. Dalton Trans 1768-1775
24. Dupont J, de Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667-3692 (Pubitemid 35353956)
25. Calò V, Nacci A, Monopoli A (2006) Effects of ionic liquids on Pd-catalysed carbon-carbon bond formation. Eur J Org Chem 2006:3791-3802
26. Cassol CC, Umpierre AP, Machado G, Wolke SI, Dupont J (2005) The role of Pd nanoparticles in ionic liquid in the heck reaction. J Am Chem Soc 127:3298-3299 (Pubitemid 40365267)
27. Fonseca GS, Umpierre AP, Fichtner PF, Teixeira SR, Dupont J (2003) The use of imidazolium ionic liquids for the formation and stabilization of ir0 and rh0 nanoparticles: efficient catalysts for the hydrogenation of arenes. Chem Eur J 9:3263-3269
28. Hagiwara H, Sugawara Y, Isobe K, Hoshi T, Suzuki T (2004) Immobilization of Pd(OAc)2 in ionic liquid on silica: application to sustainable Mizoroki-Heck reaction. Org Lett 6:2325-2328 (Pubitemid 38952531)
29. 2 capture by a task-specific ionic liquid. J Am Chem Soc 124:926-927 (Pubitemid 34130976)
30. Lee MK, Lee TY, Lin BJI (2003) Supramolecular liquid crystals of amide functionalized imidazolium salts. J Mater Chem 13:1079-1084
31. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Rev A.1. Gaussian Inc, Wallingford
32. Zhao Y, Schultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theor Comput 2:364-382
33. Hay JP, Wadt RW (1985) Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg. J Chem Phys 82:270-283
34. Petrović ZD, Simijonović D, Petrović VP, Marković S (2010) Diethanolamine and N, N-diethylethanolamine ionic liquids as precatalyst-precursors and reaction media in green Heck reaction protocol. J Mol Catal A Chem 327:45-50
35. Bouquillon S, du Moulinet d'Hardemare A, Averbuch-Pouchot MT, Hénin F, Muzart J, Durif A (1999) A coordinaton compound of (-) ephedrine and palladium(II). Acta Cryst C55:2028-2030