Stereospecific Pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides

Journal of the American Chemical Society

Volumn 136, Issue 40, 2014, Pages 14027-14030

  Li, Ling ^a   Zhao, Shibin ^a,b   Joshi Pangu, Amruta ^a,b   Diane, Mohamed ^a   Biscoe, Mark R ^a,b  

^a CITY COLLEGE OF NEW YORK   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CHLORIDE; CROSS COUPLING REACTIONS; STEREOSPECIFIC;

ALKYLBORON NUCLEOPHILE; ARYL CHLORIDE; CHLORIDE; NUCLEOPHILE; PALLADIUM; UNCLASSIFIED DRUG; ALKANE; BENZENE DERIVATIVE; BORON; CHLORINE;

ARTICLE; CATALYST; CROSS COUPLING REACTION; DERIVATIZATION; ELECTROPHILICITY; ISOMERIZATION; NUCLEOPHILICITY; REACTION TIME; STEREOCHEMISTRY; STEREOSPECIFICITY; STILLE REACTION; SUZUKI REACTION; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKANES; BENZENE DERIVATIVES; BORON; CATALYSIS; CHLORINE; PALLADIUM; STEREOISOMERISM;

EID: 84907943523     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508815w     Document Type: Article

References (53)

1. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004.
2. Netherton, M. R.; Fu, G. C. In Topics in Organometallic Chemistry: Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: New York, 2005; pp 85-108.
3. Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544
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. Joshi-Pangu, A.; Biscoe, M. R. Synlett 2012, 23, 1103
7. Joshi-Pangu, A.; Ganesh, M.; Biscoe, M. R. Org. Lett. 2011, 13, 1218
8. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478
9. Joshi-Pangu, A.; Ma, X.; Diane, M.; Iqbal, S.; Kribs, R. J.; Huang, R.; Wang, C.-Y.; Biscoe, M. R. J. Org. Chem. 2012, 77, 6629
10. Li, L.; Wang, C.-Y.; Huang, R.; Biscoe, M. R. Nat. Chem. 2013, 5, 607
11. Hoffman, R. W.; Hölzer, B.; Knopff, O.; Harms, K. Angew. Chem., Int. Ed. 2000, 39, 3072
12. Hölzer, B.; Hoffman, R. W. Chem. Commun. 2003, 732
13. Boudier, A.; Darcel, C.; Flachsman, F.; Micouin, L.; Oestreich, M.; Knochel, P. Chem. - Eur. J. 2000, 6, 2748
14. Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-Y. J. Am. Chem. Soc. 2006, 128, 3538
15. Thaler, T.; Haag, B.; Gavryushin, A.; Schober, K.; Hartman, E.; Gschwing, R. M.; Zipse, H.; Mayer, P.; Knochel, P. Nat. Chem. 2010, 2, 125
16. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129
17. Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1
18. Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973
19. Mohapatra, S.; Bandyopadhyay, A.; Barma, D. K.; Capdevila, J. H.; Falck, J. R. Org. Lett. 2003, 5, 4759
20. Falck, J. R.; Patel, P. K.; Bandyopadhyay, A. J. Am. Chem. Soc. 2007, 129, 790
21. Li, H.; He, A.; Falck, J. R.; Liebeskind, L. S. Org. Lett. 2011, 13, 3682
22. Kalkofen, R.; Hoppe, D. Synlett 2006, 1959
23. Lange, H.; Fröhlich, R.; Hoppe, D. Tetrahedron 2008, 64, 9123
24. ref 4d. Organosilicon reagents
25. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793
26. Denmark, S. E.; Werner, N. S. J. Am. Chem. Soc. 2010, 132, 3612
27. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024
28. Sandrock, D. L.; Jean-Gerard, L.; Chen, C.-Y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108
29. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191
30. Daini, M.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 4758
31. Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738
32. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894
33. Molander, G. A.; Wisniewski, S. R. J. Am. Chem. Soc. 2012, 134, 16856
34. Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed. 2013, 52, 3989
35. Sun, C.; Potter, B.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 6534
36. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433-6
37. Bonet, A.; Odachowski, M.; Leonori, D.; Essafi, S.; Aggarwal, V. K. Nat. Chem. 2014, 6, 584
38. Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414
39. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257
40. van der Hoogenband, A.; Lange, J. H. M.; Terpstra, J. W.; Koch, M.; Visser, G. M.; Visser, M.; Korstanje, T. J.; Jastrzebski, J. T. B. H. Tetrahedron Lett. 2008, 49, 4122
41. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020
42. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553
43. Biscoe, M. R.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 6686
44. Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073
45. Bruno, N. C.; Tudge, M. T.; Buchwald, S. L. Chem. Sci. 2013, 4, 916
46. Molander, G. A.; Sandrock, D. L. Curr. Opin. Drug Discovery Devel. 2009, 12, 811
47. Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623
48. Joshi, N. N.; Pyun, C.; Mahindroo, V.; Singaram, B.; Brown, H. C. J. Org. Chem. 1992, 57, 504
49. Lennox, A. J. J.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2012, 51, 9385
50. Matteson, D. S. Tetrahedron 1998, 54, 10555
51. Gonzalez-Bobes, F.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 5360
52. Kabalka, G. W.; Gooch, E. E. J. Org. Chem. 1980, 45, 3578
53. Larouche-Gauthier, R.; Elford, T. G.; Aggarwal, V. K. J. Am. Soc. Chem. 2011, 133, 16794