N,N-Dimethyl Glycine-Promoted Ullmann Coupling Reaction of Phenols and Aryl Halides

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3799-3802

  Ma, Dawei ^a   Cai, Qian ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLGLYCINE; ETHER; GLYCINE; HALIDE; IODIDE; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HIGH TEMPERATURE; SYNTHESIS;

CATALYSIS; HYDROCARBONS, HALOGENATED; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHENOLS; SARCOSINE;

EID: 0242543883     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0350947     Document Type: Article

References (25)

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7. For recent copper-catalyzed direct coupling reaction of aryl halides and phenols, see: (a) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623-1626. (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315-4317. (c) Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Chem. Commun. 1998, 2091-2092. (d) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
8. For recent copper-catalyzed direct coupling reaction of aryl halides and phenols, see: (a) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623-1626. (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315-4317. (c) Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Chem. Commun. 1998, 2091-2092. (d) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
9. For recent copper-catalyzed coupling reaction of arylboronic acids or arylboronates with phenols, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (b) Chen, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933-2936. (c) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. (d) Dicicco, C. P.; Song, Y. ; Evans, D. A. Org. Lett. 2001, 3, 1029-1032. (e) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142. (f) Chen, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
10. For recent copper-catalyzed coupling reaction of arylboronic acids or arylboronates with phenols, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (b) Chen, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933-2936. (c) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. (d) Dicicco, C. P.; Song, Y. ; Evans, D. A. Org. Lett. 2001, 3, 1029-1032. (e) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142. (f) Chen, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
11. For recent copper-catalyzed coupling reaction of arylboronic acids or arylboronates with phenols, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (b) Chen, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933-2936. (c) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. (d) Dicicco, C. P.; Song, Y. ; Evans, D. A. Org. Lett. 2001, 3, 1029-1032. (e) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142. (f) Chen, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
12. For recent copper-catalyzed coupling reaction of arylboronic acids or arylboronates with phenols, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (b) Chen, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933-2936. (c) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. (d) Dicicco, C. P.; Song, Y. ; Evans, D. A. Org. Lett. 2001, 3, 1029-1032. (e) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142. (f) Chen, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
13. For recent copper-catalyzed coupling reaction of arylboronic acids or arylboronates with phenols, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (b) Chen, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933-2936. (c) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. (d) Dicicco, C. P.; Song, Y. ; Evans, D. A. Org. Lett. 2001, 3, 1029-1032. (e) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142. (f) Chen, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
14. For recent copper-catalyzed coupling reaction of arylboronic acids or arylboronates with phenols, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (b) Chen, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933-2936. (c) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. (d) Dicicco, C. P.; Song, Y. ; Evans, D. A. Org. Lett. 2001, 3, 1029-1032. (e) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142. (f) Chen, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865.
15. For other recent examples, see: (a) Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169-2171. (b) Wipf, P.; Lynch, S. M. Org. Lett. 2003, 5, 1155-1158. (c) Krenitsky, P. J.; Boger, D. L. Tetrahedron Lett. 2002, 43, 407-410. (d) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986-2987. (e) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (f) Zhu, J. Synlett 1997, 133-144 and references therein. (g) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Brase, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422. (h) Zhu, J. P.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396.
16. For other recent examples, see: (a) Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169-2171. (b) Wipf, P.; Lynch, S. M. Org. Lett. 2003, 5, 1155-1158. (c) Krenitsky, P. J.; Boger, D. L. Tetrahedron Lett. 2002, 43, 407-410. (d) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986-2987. (e) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (f) Zhu, J. Synlett 1997, 133-144 and references therein. (g) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Brase, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422. (h) Zhu, J. P.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396.
17. For other recent examples, see: (a) Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169-2171. (b) Wipf, P.; Lynch, S. M. Org. Lett. 2003, 5, 1155-1158. (c) Krenitsky, P. J.; Boger, D. L. Tetrahedron Lett. 2002, 43, 407-410. (d) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986-2987. (e) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (f) Zhu, J. Synlett 1997, 133-144 and references therein. (g) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Brase, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422. (h) Zhu, J. P.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396.
18. For other recent examples, see: (a) Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169-2171. (b) Wipf, P.; Lynch, S. M. Org. Lett. 2003, 5, 1155-1158. (c) Krenitsky, P. J.; Boger, D. L. Tetrahedron Lett. 2002, 43, 407-410. (d) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986-2987. (e) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (f) Zhu, J. Synlett 1997, 133-144 and references therein. (g) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Brase, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422. (h) Zhu, J. P.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396.
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20. For other recent examples, see: (a) Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169-2171. (b) Wipf, P.; Lynch, S. M. Org. Lett. 2003, 5, 1155-1158. (c) Krenitsky, P. J.; Boger, D. L. Tetrahedron Lett. 2002, 43, 407-410. (d) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986-2987. (e) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (f) Zhu, J. Synlett 1997, 133-144 and references therein. (g) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Brase, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422. (h) Zhu, J. P.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396.
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