Palladium-catalyzed carbohalogenation: Bromide to iodide exchange and domino processes

Journal of the American Chemical Society

Volumn 133, Issue 38, 2011, Pages 14916-14919

  Newman, Stephen G ^a   Howell, Jennifer K ^a   Nicolaus, Norman ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL IODIDES; CARBON-IODINE BONDS; COMPLEX PRODUCTS; DIASTEREOSELECTIVITIES; DOMINO PROCESS; HETEROCYCLES; HIGH YIELD; MULTIPLE RING; STEREOGENIC CENTERS;

CARBON; CATALYSIS; IODINE; METAL HALIDES; POTASSIUM; POTASSIUM IODIDE;

BROMINE COMPOUNDS;

BROMINE DERIVATIVE; CARBON; IODINE DERIVATIVE; NITROGEN; OXYGEN; PALLADIUM; POTASSIUM IODIDE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ENANTIOSELECTIVITY; HALOGENATION; IODINATION; STEREOCHEMISTRY;

EID: 80053078982     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja206099t     Document Type: Article

References (37)

1. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., de Meijere, A., Eds.; Wiley: New York, 2002.
2. Ackermann, L. Chem. Rev. 2011, 111, 1315
3. C-H Activation; Yu, J.-Q.; Shi, Z., Eds.; Topics in Current Chemistry, Vol. 292; Springer: Berlin, 2010.
4. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
5. Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
6. Newman, S. G.; Lautens, M. J. Am. Chem. Soc. 2010, 132, 11416
7. Bryan, C. S.; Lautens, M. Org. Lett. 2010, 12, 2745
8. Newman, S. G.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 1778
9. Liu, H.; Li, C.; Qiu, D.; Tong, X. J. Am. Chem. Soc. 2011, 133, 6187
10. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232
11. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944
12. Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 1533
13. Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; Garcia-Fortanet, J.; Buchwald, S. L. Science 2009, 325, 1661
14. Shen, X.; Hyde, A. M.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14076
15. Li, Y.; Liu, X.; Jiang, H.; Liu, B.; Chen, Z.; Zhou, P. Angew. Chem., Int. Ed. 2011, 50, 6341
16. Li, Y.; Liu, X.; Jiang, H.; Feng, Z. Angew. Chem, Int. Ed. 2010, 49, 3338
17. Kalyani, D.; Satterfield, A. D.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 8419
18. Kalyani, D.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 2150
19. Yin, G.; Liu, G. Angew. Chem., Int. Ed. 2008, 47, 5442
20. Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142
21. Frech, C. M.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 12434
22. Klapars, A.; Buchwald., S. L. J. Am. Chem. Soc. 2002, 124, 14844
23. Metal-Catalyzed Cross-Coupling Reactions II; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
24. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
25. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176
26. Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746
27. Rene, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560
28. Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W. V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711
29. Tietze, L. F.; Kahle, K.; Raschke, T. Chem.-Eur. J. 2002, 8, 401
30. Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157
31. Grigg, R.; Santhakumar, V.; Sridharan, V. Tetrahedron Lett. 1993, 34, 3163
32. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718
33. Li, H.; Grasa, G. A.; Colacot, T. J. Org. Lett. 2010, 12, 3332
34. Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH, Weinheim, Germany, 2006.
35. Vlaar, T.; Ruijter, E.; Orru, R. V. A. Adv. Synth. Catal. 2011, 353, 809
36. Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65
37. Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365