Raising the p K a Limit of "soft" nucleophiles in palladium-catalyzed allylic substitutions: Application of diarylmethane pronucleophiles

Journal of the American Chemical Society

Volumn 135, Issue 46, 2013, Pages 17602-17609

  Sha, Sheng Chun ^a   Zhang, Jiadi ^a   Carroll, Patrick J ^a   Walsh, Patrick J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC SUBSTITUTION; CARBON NUCLEOPHILES; CONTINUING DEVELOPMENT; DIARYLMETHANE DERIVATIVES; MECHANISTIC STUDIES; PALLADIUM-CATALYZED; REACTION CONDITIONS; TSUJI-TROST REACTION;

ALLYLATION; CATALYSIS; CHEMICAL COMPOUNDS; REACTION INTERMEDIATES; SUBSTITUTION REACTIONS;

NUCLEOPHILES;

CARBON; METHANE; NUCLEOPHILE; PALLADIUM; ALLYL COMPOUND; DRUG DERIVATIVE; ORGANOMETALLIC COMPOUND;

ALKYLATION; ARTICLE; CATALYSIS; DISSOCIATION CONSTANT; HYDROGEN BOND; PROTEIN MOTIF; ROOM TEMPERATURE; SUBSTITUTION REACTION; CHEMICAL STRUCTURE; CHEMISTRY; PH;

ALLYL COMPOUNDS; CATALYSIS; HYDROGEN-ION CONCENTRATION; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 84888345379     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409511n     Document Type: Article

References (62)

1. Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384
2. Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525
3. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674
4. Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656
5. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
6. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113
7. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860
8. Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044
9. Behenna, D. C.; Liu, Y.; Yurino, T.; Kim, J.; White, D. E.; Virgil, S. C.; Stoltz, B. M. Nat. Chem. 2012, 4, 130
10. Trost, B. M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2009, 131, 18343
11. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395
12. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921
13. Trost, B. M. J. Org. Chem. 2004, 69, 5813
14. Trost, B. M.; Machacek, M. R.; Aponick, A. Acc. Chem. Res. 2006, 39, 747
15. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258
16. Watson, I. D. G.; Styler, S. A.; Yudin, A. K. J. Am. Chem. Soc. 2004, 126, 5086
17. Watson, I. D. G.; Yudin, A. K. J. Am. Chem. Soc. 2005, 127, 17516
18. Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092 and references therein
19. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545
20. Castanet, Y.; Petit, F. Tetrahedron Lett. 1979, 20, 3221
21. Keinan, E.; Roth, Z. J. Org. Chem. 1983, 48, 1769 and references therein
22. Shukla, K. H.; DeShong, P. J. Org. Chem. 2008, 73, 6283
23. Dewick, P. M. Essentials of Organic Chemistry:For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry; John Wiley & Sons, Ltd.: West Sussex, U.K., 2006.
24. Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2009, 131, 12056
25. Trost, B. M.; Thaisrivongs, D. A.; Hartwig, J. J. Am. Chem. Soc. 2011, 133, 12439
26. Bordwell, F. G.; Bares, J. E.; Bartmess, J. E.; Drucker, G. E.; Gerhold, J.; McCollum, G. J.; Van Der Puy, M.; Vanier, N. R.; Matthews, W. S. J. Org. Chem. 1977, 42, 326
27. Zhang, J.; Stanciu, C.; Wang, B.; Hussain, M. M.; Da, C.-S.; Carroll, P. J.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2011, 133, 20552
28. Das, B.; Reddy, C. R.; Kashanna, J.; Mamidyala, S. K.; Kumar, C. G. Med. Chem. Res. 2011, 21, 3321
29. Craig, C. 2-Aminothiazole Compounds Useful as Aspartyl Protease Inhibitors. WO2005US10224, 2005.
30. Burgess, L. E.; Koch, K.; Cooper, K.; Biggers, M. S.; Ramchandani, M.; Smitrovich, J. H.; Gilbert, E. J.; Bruns, M. J.; Mather, R. J.; Donovan, C. B. Bioorg. Med. Chem. Lett. 1997, 7, 1047
31. Yoshihara, H. A.; Apriletti, J. W.; Baxter, J. D.; Scanlan, T. S. Bioorg. Med. Chem. Lett. 2001, 11, 2821
32. Bellomo, A.; Zhang, J.; Trongsiriwat, N.; Walsh, P. J. Chem. Sci. 2013, 4, 849
33. Zhang, J.; Bellomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2012, 134, 13765
34. Jia, T.; Bellomo, A.; Baina, K. E.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2013, 135, 3740
35. Zheng, B.; Jia, T.; Walsh, P. J. Org. Lett. 2013, 15, 1690
36. Zheng, B.; Jia, T.; Walsh, P. J. Org. Lett. 2013, 15, 4190
37. Hajri, M.; Blondelle, C.; Martinez, A.; Vasse, J.-L.; Szymoniak, J. Tetrahedron Lett. 2013, 54, 1029
38. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995, 14, 3081
39. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456
40. Bordwell, F. G.; Matthews, W. S.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 442
41. Cook, J. W.; Moffatt, J. S. J. Chem. Soc. 1951, 2487
42. Hsin, L.-W.; Dersch, C. M.; Baumann, M. H.; Stafford, D.; Glowa, J. R.; Rothman, R. B.; Jacobson, A. E.; Rice, K. C. J. Med. Chem. 2002, 45, 1321
43. Wai, J. S.; Egbertson, M. S.; Payne, L. S.; Fisher, T. E.; Embrey, M. W.; Tran, L. O.; Melamed, J. Y.; Langford, H. M.; Guare, J. P.; Zhuang, L.; Grey, V. E.; Vacca, J. P.; Holloway, M. K.; Naylor-Olsen, A. M.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Schleif, W. A.; Gabryelski, L. J.; Young, S. D. J. Med. Chem. 2000, 43, 4923
44. Boyd, R. E.; Rasmussen, C. R.; Press, J. B.; Raffa, R. B.; Codd, E. E.; Connelly, C. D.; Li, Q. S.; Martinez, R. P.; Lewis, M. A.; Almond, H. R.; Reitz, A. B. J. Med. Chem. 2001, 44, 863
45. Griesbaum, K.; Behr, A.; Biedenkapp, D.; Voges, H.-W.; Garbe, D.; Paetz, C.; Collin, G.; Mayer, D.; Höke, H. Hydrocarbons; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2000.
46. Hoydonckx, H. E.; Van Rhijn, W. M.; Van Rhijn, W.; De Vos, D. E.; Jacobs, P. A. Furfural and Derivatives; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2000.
47. Swanston, J. Thiophene; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2000.
48. Liu, P.; Sharon, A.; Chu, C. K. J. Fluorine Chem. 2008, 129, 743
49. Hou, G.; Gosselin, F.; Li, W.; McWilliams, J. C.; Sun, Y.; Weisel, M.; O'Shea, P. D.; Chen, C.-Y.; Davies, I. W.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882
50. Kotha, S.; Manivannan, E.; Ganesh, T.; Sreenivasachary, N.; Deb, A. Synlett 1999, 10, 1618
51. Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948
52. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2944
53. Trost, B. M.; Crawley, M. L. Chem.-Eur. J. 2004, 10, 2237
54. Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. J. Am. Chem. Soc. 2000, 122, 5968
55. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545
56. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336
57. Pretot, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323
58. You, S. L.; Zhu, X. Z.; Luo, Y. M.; Hou, X. L.; Dai, L. X. J. Am. Chem. Soc. 2001, 123, 7471
59. Zheng, W. H.; Sun, N.; Hou, X. L. Org. Lett. 2005, 7, 5151
60. Trost, B. M.; Malhotra, S.; Chan, W. H. J. Am. Chem. Soc. 2011, 133, 7328
61. Trost, B. M.; Verhoeven, T. R. J. Org. Chem. 1976, 41, 3215
62. Matsushita, H.; Negishi, E.-I. J. Chem. Soc., Chem. Commun. 1982, 160