Phosphine-catalyzed anti-carboboration of alkynoates with alkyl-, alkenyl-, and arylboranes

Journal of the American Chemical Society

Volumn 136, Issue 30, 2014, Pages 10605-10608

  Nagao, Kazunori ^a   Ohmiya, Hirohisa ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS; REGIOSELECTIVITY;

ALKENYL; ALKYNOATES; B ATOMS; CARBON ATOMS; ORGANOCATALYSTS; POSITIVELY CHARGED; TRIALKYLPHOSPHINE; TRIPLE BONDS;

PHOSPHORUS COMPOUNDS;

ALIPHATIC COMPOUND; ALKENYL GROUP; ALKYNE DERIVATIVE; ALKYNOATE DERIVATIVE; ARYLBORANE DERIVATIVE; PHOSPHINE; UNCLASSIFIED DRUG;

ANTI CARBOBORATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 84905216304     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja506310v     Document Type: Article

References (45)

1. Suginome, M.; Yamamoto, A.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 6358
2. Suginome, M.; Yamamoto, A.; Murakami, M. Angew. Chem., Int. Ed. 2005, 44, 2380
3. Suginome, M.; Yamamoto, A.; Murakami, M. J. Organomet. Chem. 2005, 690, 5300
4. Suginome, M.; Yamamoto, A.; Sasaki, T.; Murakami, M. Organometallics 2006, 25, 2911
5. Suginome, M.; Shirakura, M.; Yamamoto, A. J. Am. Chem. Soc. 2006, 128, 14438
6. Suginome, M. Chem. Rec. 2010, 10, 348
7. For a review on the synthesis of multisubstituted alkenes, see: Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698
8. Mikhailov, B. M.; Bubnov, Y. N. Tetrahedron Lett. 1971, 12, 2127
9. Erdyakov, S. Y.; Ignatenko, A. V.; Potapova, T. V.; Lyssenko, K. A.; Gurskii, M. E.; Bubnov, Y. N. Org. Lett. 2009, 11, 2872 and references therein
10. For a proposed C-B oxidative addition to Ni(0) in the hydroarylation of internal alkynes with arylboronates, see: Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2001, 2688
11. Ohmiya, H.; Makida, Y.; Tanaka, T.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 17276
12. Ohmiya, H.; Makida, Y.; Li, D.; Tanabe, M.; Sawamura, M. J. Am. Chem. Soc. 2010, 132, 879
13. Ohmiya, H.; Yokobori, U.; Makida, Y.; Sawamura, M. J. Am. Chem. Soc. 2010, 132, 2895
14. Nagao, K.; Yokobori, U.; Makida, Y.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 8982
15. Yoshida, M.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 11896
16. Shido, Y.; Yoshida, M.; Tanabe, M.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 18573
17. Hojoh, K.; Shido, Y.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2014, 53, 4954
18. Wakamatsu, T.; Nagao, K.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2013, 52, 11620
19. Yamamoto, A.; Suginome, M. J. Am. Chem. Soc. 2005, 127, 15706
20. Daini, M.; Yamamoto, A.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 2918
21. Daini, M.; Suginome, M. Chem. Commun. 2008, 5224
22. Nakada, K.; Daini, M.; Suginome, M. Chem. Lett. 2013, 42, 538
23. Alfaro, R.; Parra, A.; Alemán, J.; Ruano, J. L. G.; Tortosa, M. J. Am. Chem. Soc. 2012, 134, 15165
24. Zhang, L.; Cheng, J.; Carry, B.; Hou, Z. J. Am. Chem. Soc. 2012, 134, 14314
25. Yoshida, H.; Kageyuki, I.; Takaki, K. Org. Lett. 2013, 15, 952
26. Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2001, 40, 790
27. Shimizu, M.; Nakamaki, C.; Shimono, K.; Schelper, M.; Kurahashi, T.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 12506
28. Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670
29. Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Inoue, E.; Tanemura, K.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634
30. Nishihara, Y.; Okada, Y.; Jiao, J.; Suetsugu, M.; Lan, M.-T.; Kinoshita, M.; Iwasaki, M.; Takagi, K. Angew. Chem., Int. Ed. 2011, 50, 8660
31. Endo, K.; Hirokami, M.; Shibata, T. J. Org. Chem. 2010, 75, 3469
32. Hupe, E.; Marek, I.; Knochel, P. Org. Lett. 2002, 4, 2861
33. Okuno, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2011, 50, 920
34. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
35. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
36. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
37. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
38. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. K. Nature 2008, 456, 778
39. Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2010, 49, 5142
40. Pulis, A. P.; Aggarwal, V. K. J. Am. Chem. Soc. 2012, 134, 7570
41. Aggarwal, V. K.; Binanzer, M.; Ceglie, M. C. d.; Gallanti, M.; Glasspoole, B. W.; Kendrick, S. J. F.; Sonawane, R. P.; Vázquez-Romero, A.; Webster, M. P. Org. Lett. 2011, 13, 1490
42. Partridge, B. M.; Chausset-Boissarie, L.; Burns, M.; Pulis, A. P.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2012, 51, 11795
43. Pulis, A. P.; Blair, D. J.; Torres, E.; Aggarwal, V. K. J. Am. Chem. Soc. 2013, 135, 16054
44. Ohmura, T.; Awano, T.; Suginome, M. Chem. Lett. 2009, 38, 664
45. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191