Mechanistic aspects of palladium-catalyzed allylstannylation of alkynes

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2209-2211

  Shirakawa, Eiji ^a   Yoshida, Hiroto ^b   Nakao, Yoshiaki ^b   Hiyama, Tamejiro ^b  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000171394     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0000861     Document Type: Article

References (16)

1. (a) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976.
2. (b) Shirakawa, E.; Yoshida, H.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 4290-4291.
3. (c) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
4. (a) Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513-1514.
5. (b) Matsukawa, Y.; Asao, N.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 3779-3790.
6. Miura, K.; Itoh, D.; Hondo, T.; Saito, H.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1996, 37, 8539-8542.
7. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
8. (b) Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997.
9. (c) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
10. Munz, C.; Stephan, C.; tom Dieck, H. J. Organomet. Chem. 1991, 407, 413-420.
11. No reaction between 1d and 2c occurred in the absence of the palladium catalyst (50 °C, 1 h). This result excludes a metalloene reaction pathway, which is known to take place in the case of allylstannanes and carbonyl compounds; see ref 4b.
12. Oxidative addition of allylstannanes to Pd(0) complexes has been suggested; see Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057-5058. Franks, R. J.; Nicholas, K. M. Organometallics 2000, 19, 1458-1460.
13. Oxidative addition of allylstannanes to Pd(0) complexes has been suggested; see Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057-5058. Franks, R. J.; Nicholas, K. M. Organometallics 2000, 19, 1458-1460.
14. The retention of the double bond configuration in the reaction of 1b or 1c with 2c to give E-or Z-3c/3″c′, respectively, should imply that the isomerization between syn-7/8 and anti-7/8 does not take place under the reaction conditions.
15. Trienylstannane 3″c should not be formed through a palladacyclopentadiene because a stoichiometric reaction of 2,3,4,5-tetrakis(methoxy-carbonyl)palladacyclopentadiene with crotylstannane 1b (50 °C, 24 h, in toluene) did not afford the corresponding carbostannylation product. For a palladacyclopentadiene intermediate of the palladium-catalyzed dimerization-carbostannylation of alkynes, see ref 1b.
16. Although the possibility that the reaction of 1a proceeds also through cycle B, as noted by a referee, cannot be eliminated, it would be reasonable to consider that totally a different product distribution should be ascribed to different reaction mechanisms.