Synthesis of α-iodoketals from methyl ketones via sustainable and orthogonal tandem catalysis

Organic and Biomolecular Chemistry

Volumn 11, Issue 7, 2013, Pages 1226-1233

  Yang, Yan ^a   Gao, Meng ^a   Shu, Wen Ming ^a   Wu, Liu Ming ^a   Zhang, Dong Xue ^a   Wu, An Xin ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC REACTIONS; DIRECT SYNTHESIS; KETALIZATION; METHYL KETONES; REGIO-SELECTIVE; TANDEM CATALYSIS;

IODINE; KETONES; ORGANIC COMPOUNDS;

CATALYSIS;

COPPER; IODINATED HYDROCARBON; KETONE; OXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; COPPER; HYDROCARBONS, IODINATED; KETONES; MOLECULAR STRUCTURE; OXIDES;

EID: 84873360618     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob27028e     Document Type: Article

References (46)

1. L. F. Tietze Chem. Rev. 1996 96 115 136
2. L. F. Tietze, G. Brasche and K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, p. 631
3. K. C. Nicolaou T. Montagnon S. A. Snyder Chem. Commun. 2003 551 564
4. P. J. Alaimo R. O'Brien A. W. Johnson S. R. Slauson J. M. O'Brien E. L. Tyson A.-L. Marshall C. E. Ottinger J. G. Chacon L. Wallace C. Y. Paulino S. Connell Org. Lett. 2008 10 5111 5114
5. B.-L. Yang Z.-T. Weng S.-J. Yang S.-K. Tian Chem.-Eur. J. 2010 16 718 723
6. J.-J. Cao F. Zhou J. Zhou Angew. Chem., Int. Ed. 2010 49 4976 4980
7. M. Gao Y. Yang Y.-D. Wu C. Deng W.-M. Shu D.-X. Zhang L.-P. Cao N.-F. She A.-X. Wu Org. Lett. 2010 12 4026 4029
8. Y.-P. Zhu Q.-H. Gao M. Lian J.-J. Yuan M.-C. Liu Q. Zhao Y. Yang A.-X. Wu Chem. Commun. 2011 47 12700 12702
9. N. Shindoh Y. Takemoto K. Takasu Chem.-Eur. J. 2009 15 12168 12179
10. D. E. Fogg E. N. dos Santos Coord. Chem. Rev. 2004 248 2365 2379
11. J. C. Wasilke S. J. Obrey R. T. Baker G. C. Bazan Chem. Rev. 2005 105 1001 1020
12. S. Arndt L. C. Hsieh-Wilson Org. Lett. 2003 5 4179 4182
13. Y.-Z. Liang A. H. Franz C. Newbury C. B. Lebrilla T. E. Patten Macromolecules 2002 35 3402 3412
14. D. Hesek M. Lee W. Zhang B. C. Noll S. Mobashery J. Am. Chem. Soc. 2009 131 5187 5193
15. W. R. Roush C. E. Bennett J. Am. Chem. Soc. 2000 122 6124 6125
16. A. Richter C. Hedberg H. Waldmann J. Org. Chem. 2011 76 6694 6702
17. A. P. Kozikowski P. U. Park J. Org. Chem. 1990 55 4668 4682
18. B. B. Liau M. D. Shair J. Am. Chem. Soc. 2010 132 9594 9595
19. M. Poláková N. Pitt M. Tosin P. V. Murphy Angew. Chem., Int. Ed. 2004 43 2518 2521
20. A. Caravano D. Baillieul C. Ansiaux W. Pan J. Kovensky P. Sinay S. P. Vincent Tetrahedron 2007 63 2070 2077
21. D. W. Kwon M. S. Cho Y. H. Kim Synlett 2003 959 962
22. K. Kato H. Suzuki H. Tanaka T. Miyasaka M. Baba K. Yamaguchi H. Akita Chem. Pharm. Bull. 1999 47 1256 1264
23. J. Karban J. Kroutil M. BuděŠínský J. Sýkora I. Císařová Eur. J. Org. Chem. 2009 6399 6406
24. Y. D. Vankar R. K. Saksena A. Bawa Chem. Lett. 1989 1241 1244
25. Z. Su L. A. Paquette J. Org. Chem. 1995 60 764 766
26. Z. Yang H. Cao J. Hu R. Shan B. Yu Tetrahedron 2002 59 249 254
27. C. Daubié C. Bacquet-Einhorn D. Lelandais Can. J. Chem. 1984 62 1548 1551
28. C. Giordano L. Coppi A. Restelli J. Org. Chem. 1990 55 5400 5402
29. A. Alexakis A. Commerčon C. Coulentianos J. F. Normant Tetrahedron 1984 40 715 731
30. Z. W. Just R. C. Larock J. Org. Chem. 2008 73 2662 2667
31. Y. He C. P. Junk J. J. Cawley D. M. Lemal J. Am. Chem. Soc. 2003 125 5590 5591
32. U. P. Spitz P. E. Eaton Angew. Chem., Int. Ed. 1994 33 2220 2222
33. C. D. Dobbeleer A. Ates J.-C. Vanherk I. E. Markó Tetrahedron Lett. 2005 46 3889 3893
34. C. A. Horiuchi S. Kiji Bull. Chem. Soc. Jpn. 1997 70 421 426
35. J. S. Yadav G. Kondaji M. Shiva Ram Reddy P. Srihari Tetrahedron Lett. 2008 49 3810 3813
36. G. Yin M. Gao N. She S. Hu A. Wu Y. Pan Synthesis 2007 3113 3116
37. Z. Wang G. Yin J. Qin M. Gao L. Cao A. Wu Synthesis 2008 3675 3681
38. S. Wang L. Zhang J. Am. Chem. Soc. 2006 128 8414 8415
39. P. Goswami B. Das Tetrahedron Lett. 2009 50 897 900
40. Z. Li H. Li X. Guo L. Cao R. Yu H. Li S. Pan Org. Lett. 2008 10 803 805
41. P. J. Kocieński, Protecting Groups, Thieme, 3rd edn, 2005
42. P. G. M. Wuts and T. W. Greene, Greene's Protective Groups in Organic Synthesis, John Wiley & Sons, 4th edn, 2007
43. D. Ma Q. Geng H. Zhang Y. Jiang Angew. Chem., Int. Ed. 2010 49 1291 1294
44. H. Nowothnick J. Blum R. Schomäcker Angew. Chem., Int. Ed. 2011 50 1918 1921
45. Y.-M. Ren C. Cai Tetrahedron Lett. 2008 49 7110 7112
46. B. K. Banik M. Chapa J. Marquez M. Cardona Tetrahedron Lett. 2005 46 2341 2343