Carbamoylstannation of terminal alkynes with carbamoylstannanes: catalyst-dependent regiochemical reversal

Organometallics

Volumn 19, Issue 17, 2000, Pages 3269-3271

  Hua, Ruimao ^a   Onozawa, Shun Ya ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; OXIDATION; STRUCTURE (COMPOSITION); TEMPERATURE;

CARBAMOYLSTANNANES; CARBAMOYLSTANNATION; DIISOPROPYLCARBAMOYLTRIMETHYLSTANNANE; REGIOSELECTIVITY;

ORGANOMETALLICS;

EID: 0034248709     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000423+     Document Type: Article

References (17)

1. For our recent review, see: Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395 and references therein.
2. Si-C: (a) Sakurai, H.; Imai, T. Chem. Lett. 1975, 891.
3. (b) Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461.
4. (c) Chatani, N.; Takeyasu, T.; Horiuchi, N.; Hatafusa, T. J. Org. Chem. 1988, 53, 3539.
5. Sn-C: (d) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975.
6. (e) Shirakawa, E.; Yoshida, H.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 4290.
7. Cl-C: (f) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
8. (g) Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
9. Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221.
10. For the preparation of 1, see: Lindsay, C. M.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1988, 569.
11. 33NOSn - Me 360.1349, found 360.1423.
12. Heating a toluene solution of 1 and 1-hexyne (1:1.5) at 110°C for 8 h in the absence of the catalyst afforded 4 and 5, both in 90% yield.
13. 119Sn-H could not be resolved to display separate signals. For coupling constants between tin and olefinic protons in alkenylstannane compounds, see: Leusink, A. J.; Budding, H. A.; Marsman, J. W. J. Organomet. Chem. 1967, 9, 285.
14. +, 2), 196 (4), 168 (9), 154 (27), 111 (62), 86 (100), 55 (92).
15. +, 5), 265 (1), 249 (30), 237 (1), 221 (100), 193 (50).
16. 33NOSn-Me 360.1349, found 360.1367.
17. 2SnPd: C, 35.03; H, 7.12; N, 2.55. Found: C, 35.45; H, 7.20; N, 2.36.