Regioselectivity in the intramolecular heck reaction of a series of cyclic sulfonamides: An experimental and computational study

Chemistry - A European Journal

Volumn 18, Issue 42, 2012, Pages 13379-13387

  Geoghegan, Kimberly ^a   Evans, Paul ^a   Rozas, Isabel ^b   Alkorta, Ibon ^c  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b TRINITY COLLEGE DUBLIN   (Ireland)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

catalysis; cyclization; density functional calculations; Heck reaction; palladium; regioselectivity

Indexed keywords

CARBON-CARBON BOND FORMATION; COMPUTATIONAL STUDIES; DFT CALCULATION; HECK REACTIONS; HETEROCYCLES; RING SIZES; TRANSITION STATE;

AMIDES; CATALYSIS; CYCLIZATION; DENSITY FUNCTIONAL THEORY; OLEFINS; PALLADIUM; SULFUR COMPOUNDS;

REGIOSELECTIVITY;

ALKENE; PALLADIUM; PYRROLE DERIVATIVE; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PALLADIUM; PYRROLES; STEREOISOMERISM; SULFONAMIDES;

EID: 84867208231     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201359     Document Type: Article

References (71)

1. R. F. Heck, Org. React. 1982, 27, 345-390
2. S. E. Gibson, R. Middleton, Contemp. Org. Synth. 1996, 3, 447-471
3. J. T. Link, Org. React. 2002, 60, 157-534
4. G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644-4680
5. J. P. Knowles, A. Whiting, Org. Biomol. Chem. 2007, 5, 31-44
6. N. T. S. Phan, M. Van Der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679
7. for a monograph, see: The Mizoroki-Heck Reaction (Ed.:, M. Oestreich,), Wiley, New York, 2009.
8. D. Mc Cartney, P. J. Guiry, Chem. Soc. Rev. 2011, 40, 5122-5150
9. A. B. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945-2963.
10. L. Firmansjah, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 11340-11341
11. K. S. Bloome, R. L. McMahen, E. J. Alexanian, J. Am. Chem. Soc. 2011, 133, 20146-20148.
12. W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7.
13. H. von Schenck, B. Akermark, M. Svensson, J. Am. Chem. Soc. 2003, 125, 3503-3508
14. R. J. Deeth, A. Smith, J. M. Brown, J. Am. Chem. Soc. 2004, 126, 7144-7151.
15. J. Ruan, J. Xiao, Acc. Chem. Res. 2011, 44, 614-626
16. P. Wucher, L. Caporaso, P. Roesle, F. Ragone, L. Cavallo, S. Mecking, I. Göttker-Schnetmann, Proc. Natl. Acad. Sci. USA 2011, 108, 8955-8959
17. G. K. Datta, H. von Schenk, A. Hallberg, M. Larhad, J. Org. Chem. 2006, 71, 3896-3903.
18. For an example, see:, G. K. Datta, M. Larhed, Org. Biomol. Chem. 2008, 6, 674-676.
19. O. Kwon, D. S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky, Angew. Chem. 1998, 110, 1978-1981
20. Angew. Chem. Int. Ed. 1998, 37, 1877-1880
21. B. M. Trost, H. C. Tsui, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 3534-3535
22. P. Diaz, F. Gendre, L. Stella, B. Charpentier, Tetrahedron 1998, 54, 4579-4590
23. J. W. Dankwardt, L. A. Flippin, J. Org. Chem. 1995, 60, 2312-2313
24. A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477-6487.
25. D. J. Kucera, S. J. O'Connor, L. E. Overman, J. Org. Chem. 1993, 58, 5304-5306.
26. P. Evans, T. McCabe, B. S. Morgan, S. Reau, Org. Lett. 2005, 7, 43-46
27. P. Evans, J. Org. Chem. 2007, 72, 1830-1833
28. S. Kelleher, P. Y. Quesne, P. Evans, Beilstein J. Org. Chem. 2009, 5, No. 69
29. K. Geoghegan, S. Kelleher, P. Evans, J. Org. Chem. 2011, 76, 2187-2194.
30. J. E. M. N. Klein, K. Geoghegan, N. Méral, P. Evans, Chem. Commun. 2010, 46, 937-939.
31. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321
32. A. Jutand, Pure Appl. Chem. 2004, 76, 565-576
33. for a recent example, see:, F. Proutiere, F. Schoenebeck, Angew. Chem. 2011, 123, 8342-8345
34. Angew. Chem. Int. Ed. 2011, 50, 8192-8195.
35. M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 1559-1563
36. J. G. de Vries, Dalton Trans. 2006, 421-429.
37. For an example, see:, T. Vorfalt, K. J. Wannowius, H. Plenio, Angew. Chem. 2010, 122, 5665-5668
38. Angew. Chem. Int. Ed. 2010, 49, 5533-5536, and references therein.
39. M. Beller, H. Fischer, W. A. Herrmann, K. Afele, C. Brossmer, Angew. Chem. 1995, 107, 1992-1993
40. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849
41. W. A. Herrmann, C. Brossmer, K. Afele, C. P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992
42. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
43. A. Putey, L. Joucla, L. Picot, T. Besson, B. Joseph, Tetrahedron 2007, 63, 867-879.
44. S. Lemaire-Audoire, M. Savignac, C. Dupuis, J. P. Genêt, Tetrahedron Lett. 1996, 37, 2003-2006
45. K. S. A. Vallin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 4340-4343.
46. J. E. M. N. Klein, H. Müller-Bunz, Y. Ortin, P. Evans, Tetrahedron Lett. 2008, 49, 7187-7190.
47. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066.
48. A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488-6499.
49. L. M. Chapman, B. Adams, L. T. Kilman, A. Makriyannis, Tetrahedron Lett. 2010, 51, 1517-1522.
50. A. Roglans, A. Pla-Quintana, M. Moreno-Mañas, Chem. Rev. 2006, 106, 4622-4643
51. J. G. Taylor, A. V. Moro, C. R. D. Correia, Eur. J. Org. Chem. 2011, 1403-1428
52. F. X. Felpin, L. Nassar-Hardy, F. Le Callonnec, E. Fouquet, Tetrahedron 2011, 67, 2815-2831.
53. L. Wang, P. Li, Z. Wu, J. Yan, M. Wang, Y. Ding, Synthesis 2003, 2001-2004
54. G. A. Heropoulos, S. Georgakopoulos, B. R. Steele, Tetrahedron Lett. 2005, 46, 2469-2473
55. Y. Liu, Y. Lu, M. Prashad, O. Repič, T. J. Blacklock, Adv. Synth. Catal. 2005, 347, 217-219.
56. F. A. Siqueira, J. G. Taylor, C. R. D. Correia, Tetrahedron Lett. 2010, 51, 2102-2105.
57. P. Hanson, J. R. Jones, A. B. Taylor, P. H. Walton, A. W. Timms, J. Chem. Soc. Perkin Trans. 2 2002, 1135-1150.
58. T. Cohen, A. G. Dietz, Jr., J. R. Miser, J. Org. Chem. 1977, 42, 2053-2058.
59. B. F. Sun, C. L. Wang, R. Ding, J. Y. Xu, G. Q. Lin, Tetrahedron Lett. 2011, 52, 2155-2158.
60. T. Takemoto, M. Sodeoka, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1993, 115, 8477-8478.
61. K. Kikukawa, K. Nagira, F. Wada, T. Matsuda, Tetrahedron 1981, 37, 31-36.
62. G. Mehta, S. Sengupta, Tetrahedron Lett. 1996, 37, 8625-8626
63. S. Cacchi, G. Fabrizi, A. Goggiamani, A. Sferrazza, Synlett 2009, 973-977.
64. T. Ohmura, K. Masuda, I. Takase, M. Suginome, J. Am. Chem. Soc. 2009, 131, 16624-16625.
65. C. Bäcktorp, P. O. Norrby, Dalton Trans. 2011, 40, 11308-11314, and references therein.
66. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
67. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222
68. P. C. Hariharan, J. A. Pople, Mol. Phys. 1974, 27, 209-214.
69. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310
70. T. H. Dunning, Jr., P. J. Hay, Modern Theoretical Chemistry, Vol 3 (Ed.:, H. F. Schaefer III,), Plenum, New York, 1976.
71. V. Barone, M. Cossi, J. Tomasi, J. Chem. Phys. 1997, 107, 3210-3221.