Palladium-mediated α-arylation of β-ketosulfones: Application to the synthesis of functionalized sulfonyl phenanthrenes

Tetrahedron

Volumn 71, Issue 5, 2015, Pages 782-791

  Chang, Meng Yang ^a   Chen, Yi Chia ^a   Chan, Chieh Kai ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Phenanthrenes; Photolytic scholl ring closure; Arylation; ketosulfones

Indexed keywords

BETA KETOSULFONE DERIVATIVE; FLUORIDE; IODIDE; LITHIUM; METALLOID; PALLADIUM; PHENANTHRENE DERIVATIVE; SULFONE; SULFONYL PHENANTHRENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE; ZINC FLUORIDE;

ALKYLATION; ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CROSS COUPLING REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84920735953     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.12.070     Document Type: Article

References (70)

1. N.S. Simpkins J.E. Baldwin, Sulfones in Organic Synthesis 1993 Pergamon Oxford, UK
2. B.M. Trost Comprehensive Organic Chemistry 1991 Pergamon Oxford, UK
3. A. El-Awa, M.N. Noshi, X. Mollat du Jourdin, and P.L. Fuchs Chem. Rev. 109 2009 2315
4. B.M. Trost Bull. Chem. Soc. Jpn. 61 1988 107
5. S. Patai, Z. Rappoport, and C. Stirling The Chemistry of Sulphones and Sulphoxides 1988 Wiley Chichester, UK
6. J. Pospisil, and H. Sato J. Org. Chem. 76 2011 2269
7. B. Sreedhar, and V.S. Rawat Synlett 2012 413
8. A. Kumar, and M.K. Muthyala Tetrahedron Lett. 52 2011 5368
9. N. Suryakiran, T.S. Reddy, K. Ashalatha, M. Lakshman, and Y. Venkateswarlu Tetrahedron Lett. 47 2006 3853
10. Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang, and W. Lei J. Am. Chem. Soc. 135 2013 11481
11. G.C. Tsui, Q. Glenadel, C. Lau, and M. Lautens Org. Lett. 13 2011 208
12. C. Curti, M. Laget, A.O. Carle, A. Gellis, and P. Vanelle Eur. J. Med. Chem. 42 2007 880
13. J.K. Bin, J.S. Lee, and K. Kim Org. Lett. 6 2004 4297
14. G. Zhou, P.T. Ting, and R.G. Aslanian Tetrahedron Lett. 51 2010 939
15. X. Tang, L. Huang, Y. Xu, J. Yang, W. Wu, and H. Jiang Angew. Chem., Int. Ed. 53 2014 4205
16. R. Chawla, A.K. Singh, and L.D.S. Yadav Eur. J. Org. Chem. 10 2014 2032 and cited references therein
17. A.K. Singh, R. Chawla, and L.D.S. Yadav Tetrahedron Lett. 55 2014 4742
18. X. Shi, X. Ren, Z. Ren, J. Li, Y. Wang, S. Yang, J. Gu, Q. Gao, and G. Huang Eur. J. Org. Chem. 10 2014 5083
19. J. Xuan, Z.-J. Feng, J.-R. Chen, L.-Q. Lu, and W.-J. Xiao Chem. - Eur. J. 20 2014 3045
20. W.M. Wolf J. Mol. Struct. 474 1999 113
21. Y.M. Markitanov, V.M. Timoshenko, and Y.G. Shermolovich J. Sulfur Chem. 35 2014 188
22. G.E. Vennstra, and B. Zwaneburg Synthesis 1975 519
23. J. Wildeman, and A.M. van Leusen Synthesis 1979 733
24. Y.-Y. Xie, and Z.-C. Chen Synth. Commun. 31 2001 3145
25. For the sulfonation of silyl enol ethers, see: N. Kamigata, K. Udodaira, and T. Shimizu J. Chem. Soc., Perkin Trans. 1 1997 783
26. 2-mediated reaction of diazosulfones with aldehydes, see: C.R. Holmquist, and E.J. Roskamp Tetrahedron Lett. 33 1992 1131
27. M.W. Thomsen, B.M. Handwerker, S.A. Katz, and R.B. Belser J. Org. Chem. 53 1988 906
28. B.D. Lenihan, and H. Shechter J. Org. Chem. 63 1998 2072
29. M.-Y. Chang, Y.-C. Chen, and C.-K. Chan Synlett 2014 1739
30. M.-Y. Chang, Y.-C. Chen, and C.-K. Chan Tetrahedron 70 2014 8908
31. M.-Y. Chang, Y.-J. Cheng, and Y.-R. Lu Org. Lett. 16 2014 6252
32. B.M. Trost, and D.P. Curran Tetrahedron Lett. 22 1981 1287
33. A.-L. Fan, S. Cao, and Z. Zhang J. Heterocycl. Chem. 34 1997 1657
34. S. Ou, C.-R. Cao, M. Jiang, and J.-T. Liu Eur. J. Org. Chem. 2013 6510
35. C.R. Cao, S. Ou, M. Jiang, and T.-T. Liu Org. Biomol. Chem. 12 2014 467
36. C.C.C. Johansson, and T.J. Colacot Angew. Chem., Int. Ed. 49 2010 676
37. F. Bellina, and R. Rossi Chem. Rev. 110 2010 1082
38. D.A. Culkin, and J.F. Hartwig Acc. Chem. Res. 36 2003 234
39. F. Churrucam, R. SanMartin, I. Tellitu, and E. Dominguez Org. Lett. 4 2002 1591
40. J.R. Schmink, and N.E. Leadbeater Org. Lee. 11 2009 2575 For aldehydes, see
41. H. Muratake, M. Natsume, and H. Nakai Tetrahedron 62 2006 7093
42. R. MartIin, and S.L. Buchwald Angew. Chem., Int. Ed. 46 2007 7236 For esters, see
43. W.A. Moradi, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7996
44. S. Lee, N.A. Beare, and J.F. Hartwig J. Am. Chem. Soc. 123 2001 8410 For amides, see
45. K.H. Shaughnessy, B.C. Hamann, and J.F. Hartwig J. Org. Chem. 63 1998 6546
46. S.P. Marsden, E.L. Watson, and S.A. Raw Org. Lett. 10 2008 2905 For malonates, see
47. M. Kawatsura, and J.F. Hartwig J. Am. Chem. Soc. 121 1999 1473
48. J.M. Fox, X. Huang, A. Chieffi, and S.L. Buchwald J. Am. Chem. Soc. 122 2000 1360 For α-alkoxyketones, see
49. J.H. Lee, M. Kim, and I. Kim J. Org. Chem. 79 2014 6153
50. R.-J. Li, S.-F. Pi, Y. Liang, Z.-Q. Wang, R.-J. Song, G.-X. Chen, and J.-H. Li Chem. Commun. 2010 8183 For β-ketoesters, see
51. J.A. MacKay, R.L. Bishop, and V.H. Rawal Org. Lett. 7 2005 3421
52. J.G. Zeevaart, C.J. Parkinson, and C.B. de Koning Tetrahedron Lett. 45 2004 4261 For β-ketonitriles, see
53. J. Schranck, M. Burhardt, C. Borschein, H. Neumann, T. Skrydstrup, and M. Beller Chem. - Eur. J. 20 2014 9534
54. A.V. Mitin, A.N. Kashin, and I.P. Beletskaya J. Organomet. Chem. 689 2004 1085
55. E.M. Vogl, and S.L. Buchwald J. Org. Chem. 67 2002 106 For nitriles, see
56. D.A. Culkin, and J.F. Hartwig J. Am. Chem. Soc. 124 2002 9330
57. J. You, and J.G. Verkade Angew. Chem., Int. Ed. 42 2003 5051 For sultams, see
58. O. Rene, B.P. Fauber, S. Malhotra, and H. Yajima Org. Lett. 16 2014 3468 For sulfoximines, see
59. G.Y. Cho, and C. Bolm Org. Lett. 7 2005 1351 For alkylsulfones, see
60. G. Zhou, P.C. Ting, and R.G. Aslanian Tetrahedron Lett. 51 2010 939
61. T. Jia, A. Bellomo, K.E. Baina, S.D. Dreher, and P.J. Walsh J. Am. Chem. Soc. 135 2013 3740 For sulfonamides, see
62. G. Zhou, P. Ting, R. Aslanian, and J.J. Piwinski Org. Lett. 10 2008 2517
63. A.N. Kashin, A.V. Mitin, and I.P. Beletskaya Tetrahedron Lett. 43 2002 2539
64. B. Pruger, G.E. Hofmeister, C.B. Jacobsen, D.G. Alberg, M. Nielsen, and K.A. Jorgensen Chem. - Eur. J. 16 2010 3783
65. F.G. Bordwell, W.S. Vanier, W.S. Matthews, J.B. Hendrickson, and P.L. Skipper J. Am. Chem. Soc. 97 1975 7160
66. X. Liu, and J.F. Hartwig J. Am. Chem. Soc. 126 2004 5182
67. CCDC 1015656 (1h), 1016738 (1x), 1016743 (1aa), 1019409 (1af), 1016742 (7c), 1021030 (7o), and 1016516 (7q) contain the supplementary crystallographic data for this paper. This data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: 44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk).
68. M.-Y. Chang, and M.-H. Wu Tetrahedron 69 2013 169
69. T.G. Back, S. Collins, and R.G. Kerr J. Org. Chem. 48 1983 3077
70. A.R. Katritzky, A.A.A. Abdel-Fattah, and M. Wang J. Org. Chem. 68 2003 1443