The effect of crown-ether on the palladium-catalyzed Ullmann-type coupling mediated by zinc in air and water

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4831-4834

  Venkatraman, Sripathy ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; ZINC;

AIR ANALYSIS; ARTICLE; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENVIRONMENTAL TEMPERATURE; ORGANIC CHEMISTRY; REACTION ANALYSIS; WATER ANALYSIS;

EID: 0034686194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00658-4     Document Type: Article

References (35)

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3. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9; Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980; Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
4. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9; Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980; Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
5. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9; Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980; Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
6. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9; Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980; Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
7. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9; Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980; Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
8. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9; Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980; Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
9. For Ni catalyzed Ullman-type couplings, see: Takagi, K.; Hayama, N.; Sasaki, K. Bull. Chem. Soc. Jpn. 1984, 57, 1887; Meyer, G.; Rollin, Y.; Perichon, J. J. Organomet. Chem. 1987, 333, 263.
10. For Ni catalyzed Ullman-type couplings, see: Takagi, K.; Hayama, N.; Sasaki, K. Bull. Chem. Soc. Jpn. 1984, 57, 1887; Meyer, G.; Rollin, Y.; Perichon, J. J. Organomet. Chem. 1987, 333, 263.
11. Recently, Liebeskind reported an ambient temperature Ullmann-type coupling, see: Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312 and references cited therein.
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13. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615; Tsuji, J. Topics Curr. Chem. 1980, 91, 29; Kumada, M. Pure Appl. Chem. 1980, 52, 669; Negishi, E. I. Acc. Chem. Res. 1982, 15, 340; Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669; Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985; Oppolzer, W. Angew. Chem. 1989, 101, 39; Trost, B. M. Acc. Chem. Res. 1990, 23, 34; Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
14. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615; Tsuji, J. Topics Curr. Chem. 1980, 91, 29; Kumada, M. Pure Appl. Chem. 1980, 52, 669; Negishi, E. I. Acc. Chem. Res. 1982, 15, 340; Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669; Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985; Oppolzer, W. Angew. Chem. 1989, 101, 39; Trost, B. M. Acc. Chem. Res. 1990, 23, 34; Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
15. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615; Tsuji, J. Topics Curr. Chem. 1980, 91, 29; Kumada, M. Pure Appl. Chem. 1980, 52, 669; Negishi, E. I. Acc. Chem. Res. 1982, 15, 340; Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669; Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985; Oppolzer, W. Angew. Chem. 1989, 101, 39; Trost, B. M. Acc. Chem. Res. 1990, 23, 34; Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
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17. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615; Tsuji, J. Topics Curr. Chem. 1980, 91, 29; Kumada, M. Pure Appl. Chem. 1980, 52, 669; Negishi, E. I. Acc. Chem. Res. 1982, 15, 340; Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669; Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985; Oppolzer, W. Angew. Chem. 1989, 101, 39; Trost, B. M. Acc. Chem. Res. 1990, 23, 34; Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
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32. All products are known compounds and were characterized by NMR and GC-MS. Experimental procedure: To a suspension of 4-iodotoluene (300 mg, 1.3 mmol) in 10 mL of de-ionized water in a 50 mL test-tube was added Pd/C (10%, 291 mg, 0.27 mmol), 18-crown-6 (73 mg, 0.27 mmol) and zinc powder (273 mg, 4.12 mmol). The mixture was capped and stirred overnight, diluted with 4 mL 1N aqueous HCl, filtered through Celite and washed with ether. The filtrate was extracted with ether and concentrated. The resulting crude material was passed through a short column of silica gel to give 4,4′-dimethylbiphenyl (85 mg, 68%).
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