On the catalytic cycle of the palladium-catalyzed cross-coupling reaction of alkynylstannane with aryl iodide

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5177-5180

  Shirakawa, Eiji ^a   Yoshida, Hiroto ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; ORGANOTIN COMPOUND; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030741227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01121-0     Document Type: Article

References (18)

1. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
2. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
3. (b) Mitchell, T. N. Synthesis 1992, 803.
4. (c) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 3.4; pp 200.
5. For example, see: Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
6. There have been many reports concerning oxidative addition of organostannanes to a platinum(0) complexes, which often shows the reactivities similar to palladium(O) complexes, (a) Eaborn, C.; Kundu, K.; Pidcock, A. J. Chem. Soc., Dalton Trans. 1981, 1223.
7. (b) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1979, 181, 47.
8. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, C23.
9. (d) Eaborn, C.; Pidcock, A.; Steele, B. R. J. Chem. Soc., Dalton Trans. 1976, 767.
10. (e) Cetinkaya, B.; Lappert, M. F.; McMeeking, J.; Palmer, D. E. J. Chem. Soc., Dalton Trans. 1973, 1202.
11. This type of catalytic cycle was referred without any evidence by Stille and his co-workers in the palladium-catalyzed coupling of acyl chlorides with organostannanes. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129.
12. We have already reported that the palladium complex coordinated by iminophosphine 1 is an efficient catalyst for the coupling of aryl halides with organostannanes. Shirakawa, E.; Yoshida, H.; Takaya, H. Tetrahedron Lett. in press.
13. 3IPd: C, 51.64; H, 3.82. Found: C, 51.48; H, 3.94.
14. Intermolecular exchange of an Ar group shown bellow was not observed at 25 °C in 1 d. formula presented
15. 1H} NMR (THF): δ 23.2 for 2; δ -9.2 (J = 53 Hz), 10.1 (J = 53 Hz) for 4.
16. Examination under the stoichiometric conditions revealed that transmetalation was the rate-determining-step in Cycle A, as shown by the following data. formula presented
17. The procedure for the generation of the Pd(0) complexes depicted in Figure 3 was communicated privately from Professor Tamio Hayashi (Kyoto University).
18. All attempts to isolate these complexes failed because of their instability.