Soluble and Supported Molecular CoIII Catalysts for the Regioselective Ring-Opening of 1,2-Epoxyhexane with Methanol

ChemCatChem

Volumn 5, Issue 1, 2013, Pages 201-209

  Venkatasubbaiah, Krishnan ^a,c   Feng, Yan ^a   Arrowood, Tina ^b   Nickias, Peter ^b   Jones, Christopher W ^a  

^a Georgia Institute of Technology   (United States)

^b DOW CHEMICAL COMPANY   (United States)

^c NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

Cobalt; Cooperative effects; Ligand design; Polymers; Ring opening

Indexed keywords

CATALYST DESIGNS; CATALYTIC RECYCLING; COBALT LOSS; COOPERATIVE EFFECTS; COOPERATIVITY; COUNTERIONS; HYDROLYTIC KINETIC RESOLUTION; INITIAL RATE; LIGAND DESIGN; MOLECULAR CATALYSTS; REGIO-SELECTIVE; RING OPENING; RING OPENING REACTION;

CATALYST DEACTIVATION; CATALYST SELECTIVITY; COBALT; LIGANDS; METHANOL; POLYMERS; PORPHYRINS; REACTION RATES; REGIOSELECTIVITY; SPECTROSCOPIC ANALYSIS;

CATALYST SUPPORTS;

EID: 84871667841     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200494     Document Type: Article

References (56)

1. J. Huang, T. Akita, J. Faye, T. Fujitani, T. Takei, M. Haruta, Angew. Chem. 2009, 121, 8002-8006; Angew. Chem. Int. Ed. 2009, 48, 7862-7866.
2. R. E. Parker, N. S. Isaacs, Chem. Rev. 1959, 59, 737-799.
3. J. GorzynskiSmith, Synthesis 1984, 629-656.
4. J. E. Arrowsmith, S. F. Campbell, P. E. Cross, J. K. Stubbs, R. A. Burges, D. G. Gardiner, K. J. Blackburn, J. Med. Chem. 1986, 29, 1696-1702.
5. C. Bonini, G. Righi, Synthesis 1994, 225-328.
6. G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 108, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454.
7. C. W. Johannes, M. S. Visser, G. S. Weatherhead, A. H. Hoveyda, J. Am. Chem. Soc. 1998, 120, 8340-8347.
8. E. J. Corey, F.-Y. Zhang, Angew. Chem. 1999, 111, 2057-2059; Angew. Chem. Int. Ed. 1999, 38, 1931-1934.
9. N. Kato, D. Tomita, K. Maki, M. Kanai, M. Shibasaki, J. Org. Chem. 2004, 69, 6128-6130.
10. A. K. Sinha, S. Seelan, S. Tsubota, M. Haruta, Angew. Chem. 2004, 116, 1572-1574; Angew. Chem. Int. Ed. 2004, 43, 1546-1548.
11. O. Henze, W. J. Feast, F. Gardebien, P. Jonkheijm, R. Lazzaroni, P. Leclere, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc. 2006, 128, 5923-5929.
12. M. Chini, P. Crotti, L. Favero, F. Macchia, Tetrahedron Lett. 1991, 32, 4775-4778.
13. L. RajenderReddy, M. A. Reddy, N. Bhanumathi, K. R. Rao, New J. Chem. 2001, 25, 221-222.
14. N. Iranpoor, H. Firouzabadi, A. Safavi, M. Shekarriz, Synth. Commun. 2002, 32, 2287-2293.
15. D. J. Darensbourg, R. M. Mackiewicz, A. L. Phelps, D. R. Billodeaux, Acc. Chem. Res. 2004, 37, 836-844.
16. J. S. Yadav, B. V. S. Reddy, K. Harikishan, C. Madan, A. V. Narsaiah, Synthesis 2005, 2897-2900.
17. D. J. Darensbourg, S. B. Fitch, Inorg. Chem. 2007, 46, 5474-5476.
18. D. J. Darensbourg, E. B. Frantz, Inorg. Chem. 2007, 46, 5967-5978.
19. H. Sugimoto, K. Kuroda, Macromolecules 2008, 41, 312-317.
20. D. J. Darensbourg, A. I. Moncada, Macromolecules 2009, 42, 4063-4070.
21. J. Keilitz, R. Haag, Eur. J. Org. Chem. 2009, 3272-3278.
22. A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Chem. Eur. J. 2010, 16, 8530-8536.
23. R. M. Haak, M. MartínezBelmonte, E. C. Escudero-Adán, J. Benet-Buchholza, A. W. Kleij, Dalton Trans. 2010, 39, 593-602.
24. K. K. Tanabe, S. M. Cohen, Inorg. Chem. 2010, 49, 6766-6774.
25. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938.
26. E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431.
27. J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688.
28. X. Zheng, C. W. Jones, M. Weck, Chem. Eur. J. 2006, 12, 576-583.
29. C. S. Gill, K. Venkatasubbaiah, N. T. S. Phan, M. Weck, C. W. Jones, Chem. Eur. J. 2008, 14, 7306-7313.
30. X. Zheng, C. W. Jones, M. Weck, Adv. Synth. Catal. 2008, 350, 255-261.
31. K. Venkatasubbaiah, C. S. Gill, T. Takatani, C. D. Sherrill, C. W. Jones, Chem. Eur. J. 2009, 15, 3951-3955.
32. K. Venkatasubbaiah, X. Zhu, E. Kays, K. I. Hardcastle, C. W. Jones, ACS Catal. 2011, 1, 489-492.
33. S. Jain, K. Venkatasubbaiah, C. W. Jones, R. J. Davis, J. Mol. Catal. A-Chem. 2010, 316, 8-15.
34. G. Sekar, V. K. Singh, J. Org. Chem. 1999, 64, 287-289.
35. K. Tanaka, K.-i. Otani, New J. Chem. 2010, 34, 2389-2391.
36. P.-Q. Zhao, L.-W. Xu, C.-G. Xia, Synlett 2004, 846-850.
37. M. Bandini, M. Fagioli, A. Melloni, A. Umani-Ronchi, Adv. Synth. Catal. 2004, 346, 573-578.
38. B. H. Kim, F. Piao, E. J. Lee, J. S. Kim, Y. M. Jun, B. M. Lee, Bull. Korean Chem. Soc. 2004, 25, 881-888.
39. A. Kamal, S. K. Ahmed, M. Sandbhor, M. N. A. Khan, M. Arifuddin, Chem. Lett. 2005, 34, 1142-1143.
40. M. Holbach, X. Zheng, C. Burd, C. W. Jones, M. Weck, J. Org. Chem. 2006, 71, 2903-2906.
41. S. Jain, X. Zheng, C. W. Jones, M. Weck, R. J. Davis, Inorg. Chem. 2007, 46, 8887-8896.
42. X. Zheng, C. W. Jones, M. Weck, J. Am. Chem. Soc. 2007, 129, 1105-1112.
43. M.-a. Kwon, G.-J. Kim, Catal. Today 2003, 87, 145-151.
44. S.-D. Choi, G.-J. Kim, Catal. Lett. 2004, 92, 35-40.
45. H. Yang, L. Zhang, W. Su, Q. Yang, C. Li, J. Catal. 2007, 248, 204-212.
46. H. Yang, L. Zhang, L. Zhong, Q. Yang, C. Li, Angew. Chem. 2007, 119, 6985-6989; Angew. Chem. Int. Ed. 2007, 46, 6861-6865.
47. C. S. Gill, W. Long, C. W. Jones, Catal. Lett. 2009, 131, 425-431.
48. X. Zhu, K. Venkatasubbaiah, M. Weck, C. W. Jones, J. Mol. Catal. A-Chem. 2010, 329, 1-6.
49. X. Zhu, K. Venkatasubbaiah, M. Weck, C. W. Jones, ChemCatChem 2010, 2, 1252-1259.
50. L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362.
51. L. Canali, E. Cowan, H. Deleuze, C. L. Gibson, D. C. Sherrington, J. Chem. Soc. Perkin Trans. 1 2000, 2055-2066.
52. J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377.
53. T. Belser, E. N. Jacobsen, Adv. Synth. Catal. 2008, 350, 967-971.
54. C. W. Jones, Top. Catal. 2010, 53, 942-952.
55. Y. M. Terblans, J. J. Huyser, M. Huyser, M. J. Greee, D. A. Young, M. S. Sibiya, Can. J. Chem. 2005, 83, 854-861.
56. H. Hirai, Y. Nakao, N. Toshima, Chem. Lett. 1976, 5, 905-910.