The directed ortho metalation-Ullmann connection. A new Cu(I)-catalyzed variant for the synthesis of substituted diaryl ethers

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2986-2987

  Kalinin, Alexey V ^a   Bower, Justin F ^a,b,c,d   Riebel, Peter ^a,b,c,d   Snieckus, Victor ^a,b,c,d  

^a UNIVERSITY OF WATERLOO   (Canada)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

^d QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMIDE; BENZAMIDE DERIVATIVE; ETHER DERIVATIVE; SULFONAMIDE; SULFONE; TOLUENE;

ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033617396     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990114x     Document Type: Article

References (32)

1. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
2. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
3. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
4. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
5. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
6. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
7. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
8. C-O bond formation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10640 and references therein. C-N bond formation: (b) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 and references therein. (c) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827- 828. (d) For a recent review on transition metal catalyzed synthesis of arylamines/ethers, see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067. Hartwig, J. F. Synlett 1997, 329-340. (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. C-S bond formation: (f) Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543-546. (g) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
9. For a promising new methodology of diaryl ether/amine synthesis using copper-mediated coupling of aryl boronic acids with phenols and amines, see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944. (d) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
10. For a promising new methodology of diaryl ether/amine synthesis using copper-mediated coupling of aryl boronic acids with phenols and amines, see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944. (d) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
11. For a promising new methodology of diaryl ether/amine synthesis using copper-mediated coupling of aryl boronic acids with phenols and amines, see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944. (d) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
12. For a promising new methodology of diaryl ether/amine synthesis using copper-mediated coupling of aryl boronic acids with phenols and amines, see: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944. (d) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
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14. Review: Lindley, J. Tetrahedron 1984, 40, 1433-1456. For an Ullmann reaction under ultrasound, see: Hanoun, J.-P.; Galy, J.-P.; Tenaglia, A. Synth. Commun. 1995, 25, 2443-2448. For a non-Ullmann diaryl ether synthesis, see: Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815-8824.
15. Review: Lindley, J. Tetrahedron 1984, 40, 1433-1456. For an Ullmann reaction under ultrasound, see: Hanoun, J.-P.; Galy, J.-P.; Tenaglia, A. Synth. Commun. 1995, 25, 2443-2448. For a non-Ullmann diaryl ether synthesis, see: Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815-8824.
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17. See, inter alia: Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.; Richardson, T. I.; Trotter, B. W.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2704-2708. Nicolaou, K. C.; Takayanagi, M.; Jain, N. F.; Natarajan, S.; Koumbis, A. E.; Bando, T.; Ramanjulu, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2717-2719. Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III. J. Org. Chem. 1998, 63, 6338-6343 and references therein. Boger, D. L.; Miyazaki, O. L.; Beresis, R. T.; Castle, S. L.; Wu, J. H.; Jin, Q. J. Am. Chem. Soc. 1998, 120, 8920-8926.
18. See, inter alia: Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.; Richardson, T. I.; Trotter, B. W.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2704-2708. Nicolaou, K. C.; Takayanagi, M.; Jain, N. F.; Natarajan, S.; Koumbis, A. E.; Bando, T.; Ramanjulu, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2717-2719. Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III. J. Org. Chem. 1998, 63, 6338-6343 and references therein. Boger, D. L.; Miyazaki, O. L.; Beresis, R. T.; Castle, S. L.; Wu, J. H.; Jin, Q. J. Am. Chem. Soc. 1998, 120, 8920-8926.
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