New method for C-H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction

Organic and Biomolecular Chemistry

Volumn 10, Issue 8, 2012, Pages 1587-1597

  Singh, Parvinder Pal ^a   Gudup, Satish ^a   Aruri, Hariprasad ^a   Singh, Umed ^a   Ambala, Srinivas ^a   Yadav, Mahipal ^a   Sawant, Sanghapal D ^a   Vishwakarma, Ram A ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2-METHYLTETRAHYDROFURAN; ALIPHATIC ETHERS; ARYLATIONS; CROSS COUPLING REACTIONS; CROSS-COUPLED PRODUCT; CYCLIC ETHER; MEDIATED REACTIONS; ORGANOLITHIUM SPECIES; ORGANOMETALLIC REAGENT; REGIOISOMERS; TETRA-HYDROFURAN; TETRAHYDROPYRAN;

HYDROGEN; IRON OXIDES; ORGANOMETALLICS;

ETHERS;

ETHER DERIVATIVE; FERRIC ION; FERRIC OXIDE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYLATION; CATALYSIS; ETHERS, CYCLIC; FERRIC COMPOUNDS; MOLECULAR STRUCTURE;

EID: 84857200852     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06660a     Document Type: Article

References (46)

1. J. A. Labinger J. E. Bercaw Nature 2002 417 507
2. V. Ritleng C. Sirlin M. Pfeffer Chem. Rev. 2002 102 1731
3. G. Dyker, Handbook of C-H Transformations. Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2005
4. L. C. Campeau K. Fagnou Chem. Commun. 2006 1253
5. A. R. Dick M. S. Sanford Tetrahedron 2006 62 2439
6. R. G. Bergman Nature 2007 446 391
7. D. Alberico M. E. Scott M. Lautens Chem. Rev. 2007 107 174
8. H. M. L. Davies J. R. Manning Nature 2008 451 417
9. J. C. Lewis R. G. Bergman J. A. Ellman Acc. Chem. Res. 2008 41 1013
10. B. J. Li S. D. Yang Z. J. Shi Synlett 2008 949
11. X. Chen K. M. Engle D. H. Wang J. Q. Yu Angew. Chem., Int. Ed. 2009 48 5094
12. O. Daugulis H. Q. Do D. Shabashov Acc. Chem. Res. 2009 42 1074
13. L. Ackermann R. Vicente A. R. Kapdi Angew. Chem., Int. Ed. 2009 48 9792
14. J. Q. Yu and Z. J. Shi, C-H Activation, Topics in Current Chemistry, Vol. 292, Springer, Berlin, 2010
15. D. A. Colby R. G. Bergman J. A. Ellman Chem. Rev. 2010 110 624
16. C. L. Sun H. Li D. G. Yu M. Yu X. Zhou X. Y. Lu K. Huang S. F. Zheng B. J. Li Z. J. Shi Nat. Chem. 2010 2 1044
17. B. Sezen D. Sames J. Am. Chem. Soc. 2003 125 10580
18. A. E. Shilov G. B. Shulpin Chem. Rev. 1997 97 2879
19. G. Dyker Angew. Chem., Int. Ed. 1999 38 1698
20. B. J. Li S. D. Yang Z. J. Shi Synlett 2008 949
21. B. Li Z. H. Wu Y. F. Gu C. L. Sun B. Q. Wang Z. J. Shi Angew. Chem., Int. Ed. 2011 50 1109
22. X. Chen K. M. Engle D. H. Wang J. Q. Yu Angew. Chem., Int. Ed. 2009 48 5094
23. D. H. Wang T. S. Mei J. Q. Yu J. Am. Chem. Soc. 2008 130 17676
24. C. J. Engelin P. Fristrup Molecules 2011 16 951
25. R. Jazzar J. Hitce A. Renaudat J. S. Kreutzer O. Baudoin Chem.-Eur. J. 2010 16 2654
26. N. Yoshikai A. Mieczkowski A. Matsumoto L. Ilies E. Nakamura J. Am. Chem. Soc. 2010 132 5568
27. E. Nakamura N. Yoshikai J. Org. Chem. 2010 75 6061
28. G. Kumaraswamy A. N. Murthy A. Pitchiah J. Org. Chem. 2010 75 3916
29. P. P. Singh S. Gudup S. Ambala U. Singh S. Dadhwal B. Singh S. D. Sawant R. A. Vishwakarma Chem. Commun. 2011 47 5852
30. J. W. Westley, Polyether Antibiotics: Naturally Occurring Acid Ionophores, ed. Marcel Dekker, New York, 1982
31. M. Doblem, Ionophores and their structures, Wiley-Interscience, New York, 1981
32. K. L. Erickson in Marine Natural Products, ed. P. J. Scheuer, Academic Press, New York, 1983, Vol. 5, Chapter 4, p 131
33. C. J. Moody and M. Davies in Studies in Natural Product Chemistry, ed., Ata-ur-Rahman, Elsevier, Amsterdam, 1992, Vol. 10, p 201
34. H. Suginome M. Ishikawa K. Yorita M. Ishikawa N. Shimoyama T. Sasaki K. Orito J. Org. Chem. 1995 60 3052
35. A. Furstner A. Leitner M. Mendez H. Krause J. Am. Chem. Soc. 2002 124 13856
36. C. L. Sun B. J. Li Z. J. Shi Chem. Rev. 2011 111 1293
37. J. Iqbal B. Bhatia N. K. Nayyar Chem. Rev. 1994 94 519
38. D. P. Curran Synthesis 1988 489
39. F. Minisci Acc. Chem. Res. 1975 8 165
40. E. P. Kundig and C. M. Saudan in Lewis Acids in Organic Synthesis, ed., H. Yamamoto, Wiley-VCH, Weinheim, 2000; pp 597-652
41. Z. C. Wang X. N. Wu Y. X. Zhao J. B. Ma X. L. Ding S. G. He Chem.-Eur. J. 2011 17 3449
42. G. I. Panov K. A. Dubkov E. V. Starokon Catal. Today 2006 117 148
43. M. Che A. J. Tench Adv. Catal. 1982 31 77
44. L. A. Jones S. L. Kirby D. M. Kean G. L. Campbell J. Organomet. Chem. 1985 284 159
45. D. Noda Y. Sunada T. Hatakeyama M. Nakamura H. Nagashima J. Am. Chem. Soc. 2009 131 6078
46. A. Furstner R. Martin H. Krause G. Seidel R. Goddard C. W. Lehmann J. Am. Chem. Soc. 2008 130 8773