Copper- and Manganese-Catalyzed Cross-Coupling of Organostannanes with Organic Iodides in the Presence of Sodium Chloride

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4208-4209

  Kang, Suk Ku ^a   Kim, Jae Sun ^a   Choi, Sang Chul ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000904429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970656j     Document Type: Article

References (15)

1. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
2. (b) Mitchell, T. N. Synthesis 1992, 803-815.
3. Farina, V. Pure Appl. Chem. 1996, 68, 73-78.
4. Behling, J.; Babiak, K.; Ng, J.; Campbell, A.; Moretti, R.; Koerner, M.; Lipshutz, B. J. Am. Chem. Soc. 1988, 110, 2641-2643.
5. Piers, E.; Romero, M. A. J. Am. Chem. Soc. 1996, 118, 1215-1216 and references therein.
6. Takeda, T.; Matsunaga, K.; Kabasawa, Y.; Fujiwara, T. Chem. Lett. 1995, 771-772.
7. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
8. Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1996, 117, 5973-5982.
9. In the copper-catalyzed alkylation of organomanganese chlorides, the solvent THF/NMP (1:1) was used, and the influence of N-methylpyrrolidone (NMP) was remarkable. See: Cahiez, G.; Marquais, S. Synlett 1993, 45-46.
10. In our hands, aryl bromides and inflates did not couple.
11. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
12. f = 0.25) to afford the coupled product 3f (98 mg, 85%).
13. f = 0.28) to afford the coupled product 3i (138 mg, 85%).
14. 2(10 mol %)-catalyzed coupling of organostannane 1d with iodobenzene (2c) (Table 2, entry 9, method B), we could get the product 3h in 90% yield when DMF was used as solvent instead of NMP.
15. In a control experiment for the reaction of organostannane 1d with iodobenzene (2c) (Table 2, entry 9, Method A), when organostannane 1d in NMP was added slowly for 1 h via a syringe pump, the coupled product 3h was obtained in 92% yield. However, when organostannane 1d was added in one portion, the coupled product 3h was obtained in 60% yield along with the homocoupled product 4 (34%). The cross-coupling by adding organostannane 1d slowly with DMF as solvent was also carried out to give the coupled product 3h in 88% yield.