Catalytic anti-Markovnikov hydrobromination of alkynes

Journal of the American Chemical Society

Volumn 136, Issue 24, 2014, Pages 8799-8803

  Uehling, Mycah R ^a   Rucker, Richard P ^a   Lalic, Gojko ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; REACTION INTERMEDIATES;

BORONIC ESTERS; CATALYTIC METHODS; DIASTEREO-SELECTIVITY; POTASSIUM PHENOXIDE; REACTION CONDITIONS; REACTION MECHANISM; TERMINAL ALKENES; TERMINAL ALKYNE;

HYDROCARBONS;

ALKENE; ALKENYL GROUP; ALKYNE DERIVATIVE; BORONIC ACID DERIVATIVE; BROMIDE; EPOXIDE; ESTER; ETHER DERIVATIVE; FUNCTIONAL GROUP; HALIDE; NITRILE; REAGENT;

ARTICLE; BROMINATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROBROMINATION; STEREOCHEMISTRY;

EID: 84902682674     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja503944n     Document Type: Article

References (33)

1. Metal-catalyzed cross-coupling reactions; De Meijer, A., Diederich, F., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: 2004; Vols. 1 & 2.
2. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
3. Organometallics in Synthesis, Third Manual; Schlosser, M., Ed.; John Wiley & Sons, Inc.: 2013.
4. Hunsdiecker, H.; Hunsdiecker, C. Ber. Dtsch. Chem. Ges. B 1942, 75B, 291
5. Naskar, D.; Roy, S. Tetrahedron 2000, 56, 1369
6. Corey, E. J.; Shulman, J. I.; Yamamoto, H. Tetrahedron Lett. 1970, 11, 447
7. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408
8. Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679
9. Leusink, A. J.; Budding, H. A.; Drenth, W. J. Organomet. Chem. 1968, 11, 541
10. Chen, S.-M. L.; Schaub, R. E.; Grudzinskas, C. V. J. Org. Chem. 1978, 43, 3450
11. Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857
12. Brown, H.; Hamaoka, T.; Ravindran, N.; Subrahmanyam, C.; Somayaji, V.; Bhat, N. G. J. Org. Chem. 1989, 54, 6075
13. Zweifel, G.; Miller, J. A. Org. React. 1984, 32, 1
14. Gao, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10961
15. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568
16. Ohmura, T.; Yamamoto, Y.; Miyaura, N. J. Am. Chem. Soc. 2000, 122, 4990
17. Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2005, 127, 17644
18. Sundararaju, B.; Fürstner, A. Angew. Chem., Int. Ed. 2013, 52, 14050
19. Rummelt, S. M.; Fürstner, A. Angew. Chem., Int. Ed. 2014, 53, 3626
20. Hibino, J.; Matsubara, S.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 2151
21. Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853
22. Wipf, P. Top. Organomet. Chem. 2005, 8, 1
23. Huang, Z.; Negishi, E.-i. Org. Lett. 2006, 8, 3675
24. Zhao, Y.; Snieckus, V. Org. Lett. 2013, 16, 390
25. Ahmed, F.; Forsyth, C. J. Tetrahedron Lett. 1998, 39, 183
26. Smith, A. B.; Verhoest, P. R.; Minbiole, K. P.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 4834
27. Wang, B.; Hansen, T. M.; Wang, T.; Wu, D.; Weyer, L.; Ying, L.; Engler, M. M.; Sanville, M.; Leitheiser, C.; Christmann, M.; Lu, Y.; Chen, J.; Zunker, N.; Cink, R. D.; Ahmed, F.; Lee, C.-S.; Forsyth, C. J. J. Am. Chem. Soc. 2011, 133, 1484
28. Masuda, Y.; Hoshi, M.; Arase, A. J. Chem. Soc., Perkin Trans. 1 1992, 2725
29. Whittaker, A. M.; Lalic, G. Org. Lett. 2013, 15, 1112
30. Ohishi, T.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792
31. Whittaker, A. M.; Rucker, R. P.; Lalic, G. Org. Lett. 2010, 12, 3216
32. Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. Angew. Chem., Int. Ed. 2012, 51, 3953
33. Mankad, N. P.; Laitar, D. S.; Sadighi, J. P. Organometallics 2004, 23, 3369