General allylic C-H alkylation with tertiary nucleophiles

Journal of the American Chemical Society

Volumn 136, Issue 15, 2014, Pages 5750-5754

  Howell, Jennifer M ^a   Liu, Wei ^a   Young, Andrew J ^a,b   White, M Christina ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHEMICAL COMPOUNDS; NUCLEOPHILES; PALLADIUM COMPOUNDS; SCAFFOLDS;

ACTIVATED AROMATIC; ALIPHATIC ALCOHOL; COMPLEX SCAFFOLDS; GENERAL METHOD; NATURAL PRODUCTS; REACTION CASCADES; TERMINAL OLEFINS; UNSATURATED ESTERS;

OLEFINS;

CARBON; HYDROCARBON; HYDROGEN;

ALKYLATION; CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKYLATION; CARBON; HYDROCARBONS; HYDROGEN; PROTON MAGNETIC RESONANCE SPECTROSCOPY;

EID: 84898995301     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja500726e     Document Type: Article

References (44)

1. Engle, K. M.; Yu, J.-Q.; Davies, H. M. L.; Xi, Z.; You, S.-L.; Shi, Z.-J. In Organic Chemistry: Breakthroughs and Perspectives; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2012; pp 279-333.
2. Rousseaux, S.; Liégault, B.; Fagnou, K. In Modern Tools for the Synthesis of Complex Bioactive Molecules; John Wiley & Sons, Inc.: New York, 2012; pp 1-32.
3. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
4. Chen, D. Y. K.; Youn, S. W. Chem.-Eur. J. 2012, 18, 9452
5. White, M. C. Synlett 2012, 2746
6. White, M. C. Science 2012, 335, 807
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
9. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
10. Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094
11. Catellani, M.; Motti, E.; Della Ca, N. Acc. Chem. Res. 2008, 41, 1512
12. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
13. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
14. Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q. N.; Lazareva, A. Synlett 2006, 3382
15. Campeau, L. C.; Fagnou, K. Chem. Commun. 2006, 1253
16. He, J.; Li, S.; Deng, Y.; Fu, H.; Laforteza, B. N.; Spangler, J. E.; Homs, A.; Yu, J.-Q. Science 2014, 343, 1216
17. Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346
18. Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970
19. Strambeanu, I. I.; White, M. C. J. Am. Chem. Soc. 2013, 135, 12032
20. Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274
21. Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316
22. Stang, E. M.; White, M. C. J. Am. Chem. Soc. 2011, 133, 14892
23. Braun, M. G.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 12990
24. Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090
25. Lin, S.; Song, C. X.; Cai, G. X.; Wang, W. H.; Shi, Z. J. J. Am. Chem. Soc. 2008, 130, 12901
26. Young, A. J.; White, M. C. Angew. Chem., Int. Ed. 2011, 50, 6824
27. Trost, B. M.; Hansmann, M. M.; Thaisrivongs, D. A. Angew. Chem., Int. Ed. 2012, 51, 4950
28. Trost, B. M.; Thaisrivongs, D. A.; Donckele, E. J. Angew. Chem., Int. Ed. 2013, 52, 1523
29. Hong, A. Y.; Stoltz, B. M. Eur. J. Org. Chem. 2013, 2745
30. Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2009, 48, 3224
31. Clardy, J.; Walsh, C. Nature 2004, 432, 829
32. Boldi, A. M. Curr. Opin. Chem. Biol. 2004, 8, 281
33. Chen, M. S.; White, M. C. Science 2007, 318, 783
34. Chen, M. S.; White, M. C. Science 2010, 327, 566
35. Bigi, M. A.; Reed, S. A.; White, M. C. Nat. Chem. 2011, 3, 216
36. Gormisky, P. E.; White, M. C. J. Am. Chem. Soc. 2013, 135, 14052
37. Rinner, U.; Lentsch, C.; Aichinger, C. Synthesis (Stuttgart) 2010, 3763
38. Darroch, S.; Taylor, W.; Choo, L. K.; Mitchelson, F. Eur. J. Pharmacol. 1990, 183, 1720
39. Darroch, S. A.; Taylor, W. C.; Choo, L. K.; Mitchelson, F. Eur. J. Pharmacol. 1990, 182, 131
40. Takadoi, M.; Katoh, T.; Ishiwata, A.; Terashima, S. Tetrahedron 2002, 58, 9903
41. Miller, J. H.; Aagaard, P. J.; Gibson, V. A.; Mckinney, M. J. Pharmacol. Exp. Ther. 1992, 263, 663
42. Chackalamannil, S.; Xia, Y. Expert Opin. Ther. Pat. 2006, 16, 493
43. Prakash, G. K. S.; Wang, F.; Zhang, Z.; Ni, C. F.; Haiges, R.; Olah, G. A. Org. Lett. 2012, 14, 3260
44. Wade, P. A.; Hinney, H. R.; Amin, N. V.; Vail, P. D.; Morrow, S. D.; Hardinger, S. A.; Saft, M. S. J. Org. Chem. 1981, 46, 765