Design, generation, and synthetic application of borylzincate: Borylation of aryl halides and borylzincation of benzynes/terminal alkyne

Journal of the American Chemical Society

Volumn 135, Issue 50, 2013, Pages 18730-18733

  Nagashima, Yuki ^a   Takita, Ryo ^a   Yoshida, Kengo ^b   Hirano, Keiichi ^a   Uchiyama, Masanobu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b RIKEN Center for Sustainable Resource Science   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; COCATALYST; DFT CALCULATION; ENERGY GAIN; METAL ALKOXIDES; REACTION SEQUENCES; SYNTHETIC APPLICATION; TERMINAL ALKYNE;

DESIGN FOR TESTABILITY; METAL HALIDES;

HYDROCARBONS;

ALKYNE DERIVATIVE; ORGANOBORON DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; THERMODYNAMICS;

ALKYNES; BENZENE DERIVATIVES; BORON COMPOUNDS; HALOGENS; KINETICS;

EID: 84890695200     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409748m     Document Type: Article

References (43)

1. Uchiyama, M.; Kameda, M.; Mishima, O.; Yokoyama, N.; Koike, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1998, 120, 4934
2. Uchiyama, M.; Furuyama, T.; Kobayashi, M.; Matsumoto, Y.; Tanaka, K. J. Am. Chem. Soc. 2006, 128, 8404
3. Wang, C.; Ozaki, T.; Takita, R.; Uchiyama, M. Chem.-Eur. J. 2012, 18, 3482
4. Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425
5. Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539
6. Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514
7. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748
8. Uchiyama, M.; Kobayashi, Y.; Furuyama, T.; Nakamura, S.; Kajihara, Y.; Miyoshi, T.; Sakamoto, T.; Kondo, Y.; Morokuma, K. J. Am. Chem. Soc. 2008, 130, 472
9. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802
10. Nakamura, S.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2004, 126, 11146
11. Okuda, Y.; Wakamatsu, K.; Tückmantel, W.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 4629
12. Wakamatsu, K.; Nonaka, T.; Okuda, Y.; Tückmantel, W.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1986, 42, 4427
13. Nakamura, S.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2005, 127, 13116
14. Auer, G.; Oestreic, M. Chem. Commun. 2006, 311
15. Nakamura, S.; Uchiyama, M. J. Am. Chem. Soc. 2007, 129, 28
16. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535
17. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M; Hartwig, J. F. Chem. Rev. 2010, 110, 890
18. Yamashita, M. Angew. Chem., Int. Ed. 2010, 49, 2474 and references cited therein
19. Segawa, Y.; Yamashita, M.; Nozaki, K. Science 2006, 314, 113
20. Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2008, 130, 16069
21. Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. Chem. Lett. 2008, 37, 802
22. Kajiwara, T.; Terabayashi, T.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2008, 47, 6606
23. Laitar, D. S.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196
24. Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47
25. Cid, J.; Gulyás, H.; Carbó, J. J.; Fernández, E. Chem. Soc. Rev. 2012, 41, 3558
26. Takaya, J.; Iwasawa, N. ACS Catal. 2012, 2, 1993
27. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508
28. Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447
29. Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813
30. Zhu, L.; Duquette, J.; Zhang, M. J. Org. Chem. 2003, 68, 3729
31. Fürstner, A.; Seidel, G. Org. Lett. 2002, 4, 541
32. Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359
33. Molander, G. A.; Trice, S. L. J.; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701
34. Kawamorita, S.; Ohmiya, H.; Iwai, T.; Sawamura, M. Angew. Chem., Int. Ed. 2011, 50, 8363
35. Tang, W.; Keshipeddy, S.; Zhang, Y.; Wei, X.; Savoie, J.; Patel, N. D.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2011, 13, 1366
36. Yamamoto, T.; Morita, T.; Takagi, J.; Yamakawa, T. Org. Lett. 2011, 13, 5766
37. Huang, K.; Yu, D.-G.; Zheng, S.-F.; Wu, Z.-H.; Shi, Z.-J. Chem.-Eur. J. 2011, 17, 786
38. Kleeberg, C.; Dang, L.; Lin, Z. Y.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350
39. Yamamoto, E.; Izumi, K.; Horita, Y.; Ito, H. J. Am. Chem. Soc. 2012, 134, 19997
40. Pintaric, C.; Olivero, S.; Gimbert, Y.; Chavant, P. Y.; Duñach, E. J. Am. Chem. Soc. 2010, 132, 11825
41. Yoshida, H.; Okada, K.; Kawashima, S.; Tanino, K.; Ohshita, J. Chem. Commun. 2010, 46, 1763
42. Yoshida, H.; Kawashima, S.; Takemoto, Y.; Okada, K.; Ohshita, J.; Takaki, K. Angew. Chem., Int. Ed. 2012, 51, 235
43. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211