Synthesis and characterization of β-haloalkenyl-λ3- bromanes: Stereoselective markovnikov addition of difluoro(aryl)- λ3-bromane to terminal acetylenes

Journal of the American Chemical Society

Volumn 127, Issue 30, 2005, Pages 10460-10461

  Ochiai, Masahito ^a   Nishi, Yoshio ^a   Mori, Takeshi ^a   Tada, Norihiro ^a   Suefuji, Takashi ^a   Frohn, Hermann J ^b  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKENYL GROUP; BROMINE DERIVATIVE; FLUORINE DERIVATIVE; HALOGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; BROMINATION; ISOLATION PROCEDURE; MARKOVNIKOV ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 23044467142     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051690f     Document Type: Article

References (21)

1. For recent reviews, see: (a) Ochiai, M. In Topics in Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224, p 5.
2. (b) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
3. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
4. (d) Koser, G. F. In The Chemistry of Halides, Pseudo-Halides and Azides, Supplement D2; Patai S., Rappoport, Z., Eds; Wiley: New York, 1995; Chapter 21.
5. (e) Varvoglis, A. The Chemistry of Polycoordinated Iodine; VCH: New York, 1992.
6. Okuyama, T.; Takino, T.; Sueda, T.; Ochiai, M. J. Am. Chem. Soc. 1995, 117, 3360.
7. (a) Ochiai, M. J. Organomet. Chem. 2000, 611, 494.
8. (b) Ochiai, M.; Oshima, K.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 7059.
9. (c) Okuyama, T.; Takino, T.; Sato, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275.
10. (a) Ochiai, M.; Takaoka, Y.; Nagao, Y. J. Am. Chem. Soc. 1988, 110, 6565.
11. (b) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
12. Prakash, G. K. S.; Bruce, M. R.; Olah, G. A. J. Org. Chem. 1985, 50, 2405.
13. Ochiai, M.; Nishi, Y.; Goto, S.; Shiro, M.; Frohn, H. J. J. Am. Chem. Soc. 2003, 125, 15304.
14. Ochiai, M.; Kunishima, M.; Fuji, K.; Shiro, M.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1988, 1076.
15. (a) White, E. H.; McGirk, R. H.; Aufdermarsh, C. A.; Tiwari, H. P.; Todd, M. J. J. Am. Chem. Soc. 1973, 95, 8107.
16. (b) Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem. 1995, 60, 2112.
17. 3-iodanation of terminal alkynes, see: (a) Hara, S.; Yoshida, M.; Fukuhara, T.; Yoneda, N. Chem. Commun. 1998, 965.
18. (b) Yoshida, M.; Hara, S.; Fukuhara, T.; Yoneda, N. Tetrahedron Lett. 2000, 41, 3887.
19. 2 by difluorobromane 1 during the reaction.
20. (a) Peterson, P. E.; Duddey, J. E. J. Am. Chem. Soc. 1966, 88, 4990.
21. (b) Peterson, P. E. Acc. Chem. Res. 1971, 4, 407.