A highly catalytic robust palladium catalyzed cyanation of aryl bromides

Tetrahedron Letters

Volumn 40, Issue 47, 1999, Pages 8193-8195

  Maligres, Peter E ^a   Waters, Marjorie S ^a   Fleitz, Fred ^a   Askin, David ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CYANIDE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION;

EID: 0033584917     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01707-4     Document Type: Article

References (17)

1. Ellis, G. P.; Ronmey-Alexander, T. M. Chem. Rev. 1987, 87, 779-794. House, H. O.; Fisher, W. F. J. Org. Chem. 1969, 34, 3626.
2. Ellis, G. P.; Ronmey-Alexander, T. M. Chem. Rev. 1987, 87, 779-794. House, H. O.; Fisher, W. F. J. Org. Chem. 1969, 34, 3626.
3. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synthetic Commun. 1994, 24, 887-890. Amatore, C.; Jutand, A.; Khalil, F.; Mohamed, A. M.; Mottier, L. Organometallics 1993, 12, 3168-3178. Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714-4716. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Takagi, K; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180. Sekiya, A.; Isshikawa, N. Chem. Lett. 1975, 227-228.
4. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synthetic Commun. 1994, 24, 887-890. Amatore, C.; Jutand, A.; Khalil, F.; Mohamed, A. M.; Mottier, L. Organometallics 1993, 12, 3168-3178. Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714-4716. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Takagi, K; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180. Sekiya, A.; Isshikawa, N. Chem. Lett. 1975, 227-228.
5. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synthetic Commun. 1994, 24, 887-890. Amatore, C.; Jutand, A.; Khalil, F.; Mohamed, A. M.; Mottier, L. Organometallics 1993, 12, 3168-3178. Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714-4716. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Takagi, K; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180. Sekiya, A.; Isshikawa, N. Chem. Lett. 1975, 227-228.
6. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synthetic Commun. 1994, 24, 887-890. Amatore, C.; Jutand, A.; Khalil, F.; Mohamed, A. M.; Mottier, L. Organometallics 1993, 12, 3168-3178. Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714-4716. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Takagi, K; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180. Sekiya, A.; Isshikawa, N. Chem. Lett. 1975, 227-228.
7. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synthetic Commun. 1994, 24, 887-890. Amatore, C.; Jutand, A.; Khalil, F.; Mohamed, A. M.; Mottier, L. Organometallics 1993, 12, 3168-3178. Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714-4716. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Takagi, K; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180. Sekiya, A.; Isshikawa, N. Chem. Lett. 1975, 227-228.
8. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synthetic Commun. 1994, 24, 887-890. Amatore, C.; Jutand, A.; Khalil, F.; Mohamed, A. M.; Mottier, L. Organometallics 1993, 12, 3168-3178. Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714-4716. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Takagi, K; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180. Sekiya, A.; Isshikawa, N. Chem. Lett. 1975, 227-228.
9. Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224-8228.
10. Unpublished results, Zhao, M. Department of Process Research, Merck Research Laboratories, Merck & Co. Inc., P O Box 2000, Rahway, New Jersey 07065.
11. 2.
12. 3, 1,1′-bis(di-o-tolylphosphino)ferrocene, and 2,2′-bis(di-p-tolylphosphino)- 1,1′-binaphthyl (Tol-BINAP) gave less satisfactory results.
13. 3 or DPPF as ligands resulted in either sluggish reactions or no reaction at all. Addition of salts or a copper(I) cocatalyst offered no advantage.
14. 3 or DPPF as ligands resulted in either sluggish reactions or no reaction at all. Addition of salts or a copper(I) cocatalyst offered no advantage.
15. 3PO as a solvent gave 90% conversion after 48 h, while tetramethylurea gave <50% conversion.
16. 3: C, 63.14; H, 5.30; N, 31.56. Found: C, 63.09; H, 5.19; N, 31.62.
17. Reactions were performed on 20 mmol scale in sealed ampules employing the conditions in Ref. 9 with a 72 h age. The corresponding nitriles were isolated via flash column chromatography using silica gel (Merck 70-230 mesh, ASTM).