Nickel-catalyzed carbostannylation of alkynes with allyl-, acyl-, and alkynylstannanes: Stereoselective synthesis of trisubstituted vinylstannanes [6]

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10221-10222

  Shirakawa, Eiji ^a   Yamasaki, Kenji ^b   Yoshida, Hiroto ^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

ACETYLENE; ALKYNE; NICKEL; ORGANOTIN COMPOUND; PALLADIUM; TIN DERIVATIVE; TOLUENE; TRIBUTYLTIN; VINYL DERIVATIVE;

CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; LETTER; SYNTHESIS;

EID: 0033520681     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992597s     Document Type: Letter

References (10)

1. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
2. (b) Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997.
3. (c) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
4. Multistep synthesis of trisubstituted vinylstannanes has been reported. Wang, K. K.; Chu, K.-H.; Lin, Y.; Chen, J.-H. Tetrahedron 1989, 45, 1105-1118.
5. Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513-1514.
6. Miura, K.; Itoh, D.; Hondo, T.; Saito, H.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1996, 37, 8539-8542.
7. Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976.
8. Depending on the ligand, the palladium-catalyzed carbostannylation is accompanied by dimerization of alkynes. Shirakawa, E.; Yoshida, H.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 4290-4291.
9. Configuration of the carbostannylation products was determined by NMR studies (coupling constants and NOE) of the alkenylstannanes and/or the alkenes obtained by protonolysis. For example, the stereochemistry of 3a and 4a was determined on the basis of NOE (irradiation at the methine peak) and the H-Sn coupling constant, as shown below. For the coupling constants between tin and olefinic protons in alkenylstannanes, see: Leusink, A. J.; Budding, H. A.; Marsman, J. W. J. Organomet. Chem. 1967, 9, 285-294. (figure presented)
10. Negishi, E.; Miller, J. A. J. Am. Chem. Soc. 1983, 105, 6761-6763.