Multifunctional cyclodextrin-based N,N-bidentate ligands for aqueous Heck arylation

Applied Catalysis A: General

Volumn 479, Issue , 2014, Pages 1-8

  Potier, Jonathan ^a,b   Menuel, Stéphane ^a,b   Rousseau, Jolanta ^a,b   Tumkevicius, Sigitas ^c   Hapiot, Frédéric ^a,b   Monflier, Eric ^a,b  

^a UNIV LILLE   (France)

^b UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

^c VILNIUS UNIVERSITY   (Lithuania)

Author keywords

Aqueous catalysis; Cyclodextrins; Heck reaction; Palladium

Indexed keywords

CATALYSIS; CATALYSTS; CYCLODEXTRINS; LIGANDS; PALLADIUM; SYNTHESIS (CHEMICAL);

AEROBIC CONDITION; AQUEOUS CATALYSIS; AQUEOUS MEDIUM; COUPLING PRODUCT; HECK ARYLATION; HECK REACTIONS; NMR MEASUREMENTS; WATER SOLUBLE CATALYST;

PALLADIUM COMPOUNDS;

EID: 84899921941     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2014.04.021     Document Type: Article

References (56)

1. M. Oestreich The Mizoroki-Heck Reaction 2009 Wiley Chichester, UK
2. S. Bräse, and A. de Meijere A. de Meijere, S. Bräse, M. Oestreich, Metal-Catalyzed Cross-Coupling Reactions and More 2014 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim, Germany
3. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
4. A.B. Donnay, and L.E. Overman Chem. Rev. 103 2003 2945 2963
5. J.G. de Vries Can. J. Chem. 79 2001 1086 1092
6. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem. Int. Ed. 44 2005 4442 4489
7. D.A. Alonso, and C. Nájera S. Kobayashi, Science of Synthesis. Water in Organic Synthesis vol. 2011/7 2012 George Thieme Verlag KG Stuttgart 535 578
8. A.H.M. de Vries, J.M.C.A. Mulders, J.H.M. Mommers, H.J.W. Henderickx, J.G. de Vries, T. Asefa, A.V. Biradar, S. Das, K.K. Sharma, and R. Silva V. Polshettiwar, T. Asefa, Nanocatalysis Synthesis and Applications 2013 John Wiley & Sons, Inc. Hoboken, NJ, USA
9. M. Pagliaro, V. Pandarus, R. Ciriminna, F. Béland, and P. Demma Carà Chem. Cat. Chem. 4 2012 432 445
10. N.T.S. Phan, M. Van Der Sluys, and C.W. Jones Adv. Synth. Catal. 348 2006 609 679
11. V. Farina Adv. Synth. Catal. 346 2004 1553 1582 (and references therein)
12. B.M. Bhanage, S. Fujita, and M. Arai J. Organomet. Chem. 687 2003 211 218
13. F. Bellina, and C. Chiappe Molecules 15 2010 2211 2245
14. C. Santos, J. Barata, A. Faustino, C. Lodeiro, and G. Neves RSC Adv. 3 2013 19219 19238
15. D.K. Morita, D.R. Pesiri, S.A. David, W.H. Glaze, and W. Tumas Chem. Commun. 1998 1397 1398
16. M.A. Carroll, and A.B. Holmes Chem. Commun. 1998 1395 1396
17. B.M. Bhanage, Y. Ikushima, M. Shirai, and M. Arai Tetrahedron Lett. 40 1999 6427 6430
18. Y. Wang, Q. Yang, L. Yang, J. Shi, and M. Zhang RSC Adv. 3 2013 21251 21255
19. S.B. Solabannavar, U.V. Desai, and R.B. Mane Green Chem. 4 2002 347 348
20. J. Yang, D. Wang, W. Liu, X. Zhang, F. Bian, and W. Yu Green Chem. 15 2013 3429 3437
21. C.-J. Li Chem. Rev. 105 2005 3095 3165
22. S. Sengupta, and S. Bhattacharya J. Chem. Soc. Perkin Trans. 1 1993 1943
23. H. Hagiwara, Y. Sugawara, T. Hoshi, and T. Suzuki Chem. Commun. 21 2005 2942 2944
24. B.M. Bhanage, F.G. Zhao, M. Shirai, and M. Arai Tetrahedron Lett. 39 1998 9509 9512
25. L.R. Moore, and K.H. Shaughnessy Org. Lett. 6 2004 225 228
26. B.H. Lipshutz, and B.R. Taft Org. Lett. 10 2008 1329 1332
27. S. Yaşar, E.Ö. Özcan, N. Gürbüz, B. Çetinkaya, and İ. Özdemir Molecules 15 2010 649 659
28. T. Mizoroki, K. Mori, and A. Ozaki Bull. Chem. Soc. Jpn. 44 1971 581
29. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320 2322
30. R.F. Heck Org. React. 27 1982 345 390
31. S.M. Wong, C.M. So, and F.Y. Kwong Synlett 8 2012 1132 1153
32. T. Mahamo, M.M. Mogorosi, J.R. Moss, S.F. Mapolie, J.C. Slootweg, K. Lammertsma, and G.S. Smith J. Organomet. Chem. 703 2012 34 42
33. M. Oestreich Angew. Chem. Int. Ed. 53 2014 2282 2285
34. A. Barbosa, E. Rosinova, J. Dempsey, and A.M. Bonin Environ. Mol. Mutagen. 24 1994 81 88
35. B. Stewart, A. Harriman, and L.J. Higham Organometallics 30 2011 5338 5343
36. A.S. Gruber, D. Pozebon, A.L. Monteiro, and J. Dupont Tetrahedron Lett. 42 2001 7345 7348
37. T. Mino, Y. Shirae, Y. Sasai, M. Sakamoto, and T. Fujita J. Org. Chem. 71 2006 6834 6839
38. M.R. Buchmeiser, and K. Wurst J. Am. Chem. Soc. 121 1999 11101 11107
39. M.R. Buchmeiser, T. Schareina, R. Kempe, and K. Wurst J. Organomet. Chem. 634 2001 39 46
40. T. Kawano, T. Shinomaru, and I. Ueda Org. Lett. 4 2002 2545 2547
41. C. Najera, J. Gil-Moito, S. Karlstrum, and L.R. Falvello Org. Lett. 5 2003 1451 1454
42. A.K. Gupta, C.H. Song, and C.H. Oh Tetrahedron Lett. 45 2004 4113 4116
43. C.L. Li Chem. Rev. 105 2005 3095 3165
44. S. Iyer, G.M. Kulkarni, and C. Ramesh Tetrahedron 60 2004 2163 2172
45. X. Cui, Z. Li, C.-Z. Tao, Y. Xu, J. Li, L. Liu, and Q.-X. Guo Org. Lett. 8 2006 2467 2470
46. H. Bricout, F. Hapiot, A. Ponchel, S. Tilloy, and E. Monflier Curr. Org. Chem. 14 2010 1296 1307
47. Randomly methylated β-CDs derivatives have been preferred to unmodified β-CDs due to their higher water-solubility. See: W. Cai, T. Sun, X. Shao, and C. Chipot Phys. Chem. Chem. Phys. 10 2008 3236 3243
48. M. Ferreira, F.X. Legrand, C. Machut, H. Bricout, S. Tilloy, and E. Monflier Dalton Trans. 41 2012 8643 8647
49. A. Cassez, N. Kania, F. Hapiot, S. Fourmentin, E. Monflier, and A. Ponchel Catal. Commun. 9 2008 1346 1351
50. M. Mourer, F. Hapiot, S. Tilloy, E. Monflier, and S. Menuel Eur. J. Org. Chem. 2008 5723 5730
51. M. Mourer, F. Hapiot, E. Monflier, and S. Menuel Tetrahedron 64 2008 7159 7163
52. F. Hapiot, H. Bricout, S. Tilloy, and E. Monflier Eur. J. Inorg. Chem. 2012 1571 1578
53. C.Y. Huang Methods Enzymol. 87 1982 509 525
54. M. Espinal, J. Pons, J. Garcia-Anton, X. Solans, M. Font-Bardia, and J. Ros Inorg. Chim. Acta 361 2008 2648 2658
55. P. Srinivas, P.R. Likhar, H. Maheswaran, B. Sridhar, K. Ravikumar, and M.L. Kantam Chemistry 15 2009 1578 1581
56. J. Andrieu, J.-M. Camus, P. Richard, R. Poli, L. Gonsalvi, F. Vizza, and M. Peruzzini Eur. J. Inorg. Chem. 2006 51 68