Silver-catalyzed highly regioselective formal hydroboration of alkynes

Organic Letters

Volumn 16, Issue 13, 2014, Pages 3512-3515

  Yoshida, Hiroto ^a,b   Kageyuki, Ikuo ^a   Takaki, Ken ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84903729576     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501465x     Document Type: Article

References (43)

1. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
2. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
3. Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275
4. Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2011.
5. Yun, J. Asian J. Org. Chem. 2013, 2, 1016
6. Semba, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Chem.-Eur. J. 2012, 18, 4179
7. Yuan, W.; Ma, S. Org. Biomol. Chem. 2012, 10, 7266
8. Moure, A. L.; Arrayás, R. G.; Cárdenas, D. J.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 2012, 134, 7219
9. Park, J. K.; Ondrusek, B. A.; McQuade, D. T. Org. Lett. 2012, 14, 4790
10. Jung, H.-Y.; Yun, J. Org. Lett. 2012, 14, 2606
11. Yuan, W.; Ma, S. Adv. Synth. Catal. 2012, 354, 1867
12. Kubota, K.; Yamamoto, E.; Ito, H. J. Am. Chem. Soc. 2013, 135, 2635
13. Semba, K.; Shiomiya, M.; Fujihara, T.; Terao, J.; Tsuji, Y. Chem.-Eur. J. 2013, 19, 7125
14. Meng, F.; Jung, B.; Haeffner, F.; Hoveyda, A. H. Org. Lett. 2013, 15, 1414
15. Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2013, 135, 4934
16. Semba, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Angew. Chem., Int. Ed. 2013, 52, 12400
17. Sakae, R.; Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 1228
18. Yoshida, H.; Kawashima, S.; Takemoto, Y.; Okada, K.; Ohshita, J.; Takaki, K. Angew. Chem., Int. Ed. 2012, 51, 235
19. Takemoto, Y.; Yoshida, H.; Takaki, K. Chem.-Eur. J. 2012, 18, 14841
20. Yoshida, H.; Kageyuki, I.; Takaki, K. Org. Lett. 2013, 15, 952
21. Yoshida, H.; Shinke, A.; Takaki, K. Chem. Commun. 2013, 49, 11671
22. Kageyuki, I.; Yoshida, H.; Takaki, K. Synthesis DOI: 10.1055/s-0033- 1341267.
23. Yoshida, H.; Takemoto, Y.; Takaki, K. Chem. Commun. DOI: 10.1039/C4CC01757A.
24. Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350
25. Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang, J.; Liu, J.-H.; Fu, Y.; Czyzewaka, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 528
26. Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890
27. Laitar, D. S.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196
28. Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710
29. Ramírez, J.; Corberán, R.; Sanaú, M.; Peris, E.; Fernández, E. Chem. Commun. 2005, 3056
30. Coinage Metals in Organic Synthesis; Lipshutz, B.; Yamamoto, Y., Eds.; Chem. Rev. 2008, 108, 2793.
31. Silver in Organic Chemistry; Harmata, M., Ed.; Wiley: Hoboken, NJ, 2010.
32. Yamamoto, Y. J. Org. Chem. 2007, 72, 7817
33. Edwards, D. A.; Longley, M. J. Inorg. Nucl. Chem. 1978, 40, 1599
34. Edwards, D. A.; Harker, R. M.; Mahon, M. F.; Molloy, K. C. Inorg. Chim. Acta 2002, 328, 134
35. Visbal, R.; Laguna, A.; Gimeno, M. C. Chem. Commun. 2013, 49, 5642
36. Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47
37. Jang, H.; Zhugralin, A. R.; Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 7859
38. Sasaki, Y.; Horita, Y.; Zhong, C.; Sawamura, M.; Ito, H. Angew. Chem., Int. Ed. 2011, 50, 2778
39. Lillo, V.; Bonet, A.; Fernández, E. Dalton Trans. 2009, 2899
40. Schiffner, J. A.; Müther, K.; Oestreich, M. Angew. Chem., Int. Ed. 2010, 49, 1194
41. Calow, A. D. J.; Whiting, A. Org. Biomol. Chem. 2012, 10, 5485
42. For a computational study, see: Cid, J.; Carbó, J. J.; Fernández, E. Chem.-Eur. J. 2012, 18, 12794
43. Lee, J.-E.; Kwon, J.; Yun, J. Chem. Commun. 2008, 733