Direct alkenylation of arylamines at the ortho-position with magnesium alkylidene carbenoids and some theoretical studies of the reactions

Tetrahedron

Volumn 61, Issue 43, 2005, Pages 10262-10276

  Satoh, Tsuyoshi ^a   Ogino, Yumi ^a   Ando, Kaori ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

Alkenylation; Magnesium alkylidene carbenoid; ortho Alkenylated arylamine; Sulfoxide magnesium exchange reaction; Theoretical study

Indexed keywords

AROMATIC AMINE; CARBENOID; CHLORINE; KETONE; MAGNESIUM; MAGNESIUM CHLORIDE; SULFOXIDE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

EID: 25144445852     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.035     Document Type: Article

References (34)

1. D.H.R. Barton, and W.D. Ollis I.O. Sutherland Comprehensive Organic Chemistry Vol. 2 1979 Pergamon Oxford 131 184
2. A. Arienti, F. Bigi, R. Maggi, E. Marzi, P. Moggi, M. Rastelli, G. Sartori, and F. Tarantola Tetrahedron 53 1997 3795 3804
3. M. Yamaguchi, M. Arisawa, and M. Hirama Chem. Commun. 1998 1399 1400
4. M. Yamaguchi, and M. Arisawa Farumashia 35 1999 145 149
5. T. Satoh, T. Kawashima, S. Takahashi, and K. Sakai Tetrahedron 59 2003 9599 9607
6. T. Satoh, K. Takano, H. Someya, and K. Matsuda Tetrahedron Lett. 36 1995 7097 7100
7. T. Satoh J. Synth. Org. Chem. Jpn. 54 1996 481 489
8. T. Satoh J. Synth. Org. Chem. Jpn. 61 2003 98 110
9. T. Satoh Chem. Rec. 3 2004 329 341
10. T. Satoh, K. Takano, H. Ota, H. Someya, K. Matsuda, and M. Koyama Tetrahedron 54 1998 5557 5574
11. T. Satoh, T. Sakamoto, and M. Watanabe Tetrahedron Lett. 43 2002 2043 2046
12. T. Satoh, T. Sakamoto, M. Watanabe, and K. Takano Chem. Pharm. Bull. 51 2003 966 970
13. Preliminary results of this study was reported as a communication: T. Satoh, Y. Ogino, and M. Nakamura Tetrahedron Lett. 45 2004 5785 5789
14. P.J. Stang Chem. Rev. 78 1978 383 405
15. A. Oku, and T. Harada J. Synth. Org. Chem. Jpn. 44 1986 736 755
16. A. Oku J. Synth. Org. Chem. Jpn. 48 1990 710 723
17. W. Kirmse Angew. Chem., Int. Ed. 36 1997 1164 1170
18. M. Duraisamy, and H.M. Walborsky J. Am. Chem. Soc. 106 1984 5035 5037
19. H.M. Walborsky, and M. Duraisamy Tetrahedron Lett. 26 1985 2743 2746
20. J. Rachon, V. Goedken, and H.M. Walborsky J. Am. Chem. Soc. 108 1986 7435 7436
21. M. Topolski, M. Duraisamy, J. Rachon, J. Gawronski, K. Gawronska, V. Goedken, and H.M. Walborsky J. Org. Chem. 58 1993 546 555
22. T. Harada, Y. Nozaki, Y. Yamaura, and A. Oku J. Am. Chem. Soc. 107 1985 2189 2190
23. A. Oku, T. Harada, K. Hattori, Y. Nozaki, and Y. Yamaura J. Org. Chem. 53 1988 3089 3098
24. H. Yanagisawa, K. Miura, M. Kitamura, K. Narasaka, and K. Ando Bull. Chem. Soc. Jpn. 76 2003 2009 2026
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; G. Petersson, A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng. C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian Inc., Pittsburgh PA, 1998.
26. For both Mg and Li, the 6-31G* basis set was used.
27. D. Seebach, H. Siegel, K. Müllen, and K. Hiltbrunner Angew. Chem., Int. Ed. Engl. 18 1979 784 785
28. D. Seebach, H. Siegel, J. Gabriel, and R. Hässig Helv. Chim. Acta 63 1980 2046 2053
29. D. Seebach, R. Hässig, and J. Gabriel Helv. Chim. Acta 66 1983 308 337
30. P.v.R. Schleyer, T. Clark, A.J. Kos, G.W. Spitznagel, C. Rohde, D. Arad, K.N. Houk, and N.G. Rondan J. Am. Chem. Soc. 106 1984 6467 6475
31. A. Pelter, J. Kvicala, and D.E. Parry J. Chem. Soc., Perkin Trans. 1 1995 2681 2682
32. B. Wang, and C. Deng Chem. Phys. Lett. 147 1988 99 104
33. The electrostatic potential-derived charges using the CHelpG scheme of Breneman: E-25, -0.118; Z-25, -0.138; 24, -0.141; 26, -0.28. The Mulliken charges: E-25, +0.13; Z-25, +0.14; 24, -0.11; 26, -0.19.
34. T. Satoh, and H. Ota Tetrahedron 56 2000 5113 5122