Reductive coupling of aromatic N,N-acetals using zinc and chlorotrimethylsilane

Tetrahedron Letters

Volumn 52, Issue 27, 2011, Pages 3467-3469

  Hatano, Bunpei ^a   Tachikawa, Tomoharu ^a   Mori, Tetsunori ^a   Nagahashi, Keita ^a   Kijima, Tatsuro ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CHLOROTRIMETHYLSILANE; ZINC;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REDUCTION;

EID: 79957936543     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.104     Document Type: Article

References (21)

1. For reviews, see: R.M. de Figueiredo Angew. Chem., Int. Ed. 48 2009 1190 1193
2. S.R.S.S. Kotti, C. Timmons, and G. Li Chem. Biol. Drug Des. 67 2006 101 114
3. D. Lucet, T. Le Gall, and C. Mioskowski Angew. Chem., Int. Ed. 37 1998 2580 2627
4. For a recent review on reductive coupling of imine, see: V. Faugeroux, and Y. Genisson Curr. Org. Chem. 12 2008 751 773
5. B. Hatano, K. Nagahashi, and S. Habaue Chem. Lett. 36 2007 1418 1419
6. The use of chlorotrimethylsilane in the presence of zincs is effective for the reductive coupling of aromatic aldehydes, see: J.-H.S. Park, and P. Boudjouk J. Org. Chem. 53 1988 5871 5875
7. Only two references were reported for the reductive coupling of N,N-acetals using low valent titanium, see: C. Betschart, B. Schmidt, and D. Seebach Helv. Chim. Acta 71 1988 1999 2021
8. C. Betschart, and D. Seebach Helv. Chim. Acta 70 1987 2215 2231
9. 3N = 99:1, 97:3, 95:5, 100 mL × each). The results are presented in Tables 1 and 2, Schemes 2 and 4. The physical data of diamine 2 are available as Supplementary data.
10. When N,N-acetal 1 was treated with appropriate alkyl bromide in the presence of zinc and chlorotrimethylsilane, the corresponding alkylation product was obtained instead of diamine 2, see: B. Hatano, K. Nagahashi, and T. Kijima J. Org. Chem. 73 2008 9188 9191
11. References for activation of zinc by TMSCl, see: G. Picotin, and P. Miginiac J. Org. Chem. 52 1987 4796 4798
12. J.K. Gawronsky Tetrahedron Lett. 25 1984 2605 2608
13. X.-F. Duan, J. Zeng, J.W. Lü, and Z.-B. Zhang J. Org. Chem. 71 2006 9873 9876
14. J.E. McMurry Chem. Rev. 89 1989 1513 1524
15. B.E. Kahn, and R.D. Rieke Chem. Rev. 88 1988 733 745
16. T. Hirao, B. Hatano, Y. Imamoto, and A. Ogawa J. Org. Chem. 64 1999 7665 7667
17. B. Hatano, A. Ogawa, and T. Hirao J. Org. Chem. 63 1998 9421 9424
18. For a recent review for the reductive coupling of carbonyl compounds and references cited therein, see: A. Chatterjee, and N.N. Joshi Tetrahedron 62 2006 12137 12158
19. The NMR study of iminium salt 3 was reported, see: H. Mayr, A.R. Ofial, E.-U. Würthwein, and N.C. Aust J. Am. Chem. Soc. 1997 12727 12733
20. 1H NMR showed a week and broad signal at δ 10.6 ppm, which was assigned to 3a, along with the broadening signals of 1a.
21. In reductive coupling of N,O-acetals in the presence of titanium(IV) iodide and zinc, diamines were obtained, see: N. Yoshimura, and T. Mukaiyama Chem. Lett. 2001 1334 1335