Polymer-supported palladacycles: Efficient reagents for synthesis of benzopyrans with palladium recovery. Relationship among resin loading, Pd:P ratio, and reactivity of immobilized palladacycles

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 231-235

  Hershberger, John C ^a   Zhang, Lei ^a   Lu, Genliang ^a   Malinakova, Helena C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; PALLADIUM; PHOSPHORUS;

BENZOPYRANS; OXAPALLADACYCLES; SWELLING CAPACITIES;

POLYSTYRENES;

1,2 PROPADIENE DERIVATIVE; BENZOPYRAN DERIVATIVE; DIVINYLBENZENE; PALLADIUM; PHOSPHORUS; POLYSTYRENE DERIVATIVE; PROPIONIC ACID DERIVATIVE; REAGENT; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; IMMOBILIZATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

BENZOPYRANS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM;

EID: 31144433134     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052105w     Document Type: Article

References (50)

1. (a) Graden, H.; Kann, N. Curr. Org. Chem. 2005, 9, 733.
2. (b) Delgado, M.; Janda, K. D. Curr. Org. Chem. 2002, 6, 1031.
3. (a) Shuttleworth, S. J.; Connors, R. V.; Fu, J.; Liu, J.; Lizarzaburu, M. E.; Qiu, W.; Sharma, R.; Wanska, M.; Zhang, A. J. Curr. Med. Chem. 2005, 12, 1239.
4. (b) Danieli, B.; Giovanelli, P.; Lesma, G.; Passerella, D.; Sacchetti, A.; Silvano, A. J. Comb. Chem. 2005, 7, 458.
5. For the use of polymer-supported transition-metal complexes as stoichiometric reagents, see: (a) Barluenga, J. de Prado, A.; Santamaria, J.; Tomas, M. Organometalllcs 2005, 24, 3614.
6. (b) Graden, H.; Olsson, T.; Kann, N. Org. Lett. 2005, 7, 3565.
7. (c) Rigby, J. H.; Kondratenko, M. A. Org. Lett. 2001, 3, 3683.
8. For the use of polymer-supported transition-metal complexes as catalysts, see: (d) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
9. (e) Davies, H. M. L.; Walji, A. M. Org. Lett. 2005, 7, 2941.
10. (a) Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579.
11. (b) Hodge, P. Chem. Soc. Rev. 1997, 26, 417.
12. (c) Deratani, A.; Darling, G. D.; Horak, D.; Frechet, J. M. J. Macromolecules 1987, 20, 767.
13. (a) Walsh, D. P.; Pang, C.; Parikh, P. B.; Kim, Y. S.; Chang, Y. T. J. Comb. Chem. 2002, 4, 204.
14. (b) Sarin, V. K.; Kent, S. B. H.; Merrifield, R. B. J. Am. Chem. Soc. 1980, 102, 5463.
15. Zhao, L.-J.; He, H. S.; Shi, M.; Toy, P. H. J. Comb. Chem. 2004, 6, 680.
16. Barth, M.; Radenamm, J. J. Comb. Chem. 2004, 6, 340.
17. (a) Alexandratos, S. D.; Miller, D. H. J. Macromolecules 1996, 29, 8025.
18. (b) Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G. J. Org. Chem. 1983, 48, 3721.
19. (a) Jincy, J.; Magi, J.; Beena, M. J. Macromol. Sci. Part A 2003, 40, 863.
20. (b) Barrett, A. G. M.; de Miguel, Y. R. Tetrahedron 2002, 58, 3785.
21. (c) Dahan, A.; Portnoy, M. Chem. Commun. 2002, 2700.
22. (d) Grubbs, R.; Lau, C. P.; Cukier, R.; Brubaker, C. Jr. J. Am. Chem. Soc. 1977, 99, 4517.
23. (a) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825.
24. (b) Chapuis, C.; Barthe, M.; de Saint Laumer, J.-Y. Helv. Chim. Acta 2001, 84, 230.
25. (c) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615.
26. (a) Lu, G.; Portscheller, J. L.; Malinakova, H. C. Organometallics 2005, 24, 945.
27. (b) Lu, G.; Malinakova, H. C. J. Org. Chem. 2004, 69, 8266.
28. (c) Lu, G.; Malinakova, H. C. J. Org. Chem. 2004, 69, 4701.
29. (d) Portscheller, J. L.; Lilley, S. E.; Malinakova, H. C. Organometallics 2003, 22, 2961.
30. (e) Portscheller, J. L.; Malinakova, H. C. Org. Lett. 2002, 4, 3679.
31. 11d,e
32. Leadbeater, N. E. Curr. Med. Chem. 2002, 9, 2147.
33. Dahan, A.; Portnoy, M. Org. Lett. 2003, 5, 1197.
34. Herein, the swelling capacity is represented as the volume of the swollen polymer per 1 g of dry resin; see: (a) Adams, J. H.; Cook, R. M.; Hudson, D.; Jammalamadaka, V.; Lyttle, M. H.; Songster, M. F. J. Org. Chem. 1998, 63, 3706.
35. For volumetric methods, see: (b) Wilson, M. E.; Paech, K.; Zhou, W.-J.; Kurth, M. J. J. Org. Chem. 1998, 63, 5094.
36. 31P NMR on resins 2-4 did not yield spectra with sufficiently narrow lines to provide useful characterization data. IR spectra of resins 2-4 did not change upon storage.
37. The standard deviation of the ICP analysis of Pd or P was ±0.2-0.3%, translating into a precision of calculated Pd:P ratios of ±0.3 units, e.g. 1:(2.0 ± 0.3).
38. The filtrates and resin extracts from experiments described in entries 1 and 4-10 (Table 1) contained either no palladacycle 1, or only traces of palladacycle 1, and in three cases 4-12% of the total balance of palladacycle 1. The residues from experiments described in entries 2, 3, 11, and 12 (Table 1) contained 20-30% of residual palladacycle I.
39. The lower concentration of phosphine groups in resin D, as well as the presence of electron-deficient phosphine ligands bearing COOR, may account for this observation. A partial oxidation of phosphine groups in resin D during its preparation was not ruled out.
40. 2 in benzopyran 6 (see Table 2).
41. Isomerization of benzopyran 5 into 6 at elevated temperatures in solution required the presence of free phosphine and/or palladacycle (see the Supporting Information).
42. 3) with dimethyl acetylenedicarboxylate (3.0 equiv) in solution were inhibited by an excess of phosphine (see the Supporting Information).
43. Palladacycles immobilized on Tentagel resins could only be obtained as spongelike materials retaining solvent, undergoing oxidation, and rapidly releasing palladium(0).
44. 3). For effects of the conformational flexibility of immobilized ligands, see: Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051.
45. -1); see: Greaves, E. O.; Lock, C. J. L.; Maitlis, P. L. M. Can. J. Chem. 1968, 46, 3879.
46. Palladium(0) from solution-phase reactions could not be efficiently removed by the use of 3-mercaptopropyl-functionalized silica gel. For Pd scavenging see: Crudden, C. M.: Sateesh, M.; Lewis, R. J. Am. Chem. Soc. 2005, 127, 10045.
47. (a) Ahlquist, M.; Fabrizi, G.; Cacchi, C.; Norrby, P.-O. Chem. Commun. 2005, 4196.
48. (b) IR data recorded on resins E-G are provided and discussed in the Supporting Information.
49. Ziegert, R. E.; Torang, Knepper, K.; Brase, S. J. Comb. Chem. 2005, 7, 147.
50. For palladium(0)-catalyzed dimerization of allenes, see: Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615.