Copper(I)-mediated novel thiocyanation of nonactivated aryl iodides

Synthetic Communications

Volumn 26, Issue 18, 1996, Pages 3413-3419

  Suzuki, Hitomi ^a   Abe, Hajime ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029839078     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003745     Document Type: Article

References (38)

1. For general survey of thiocyanates, see: a) Harusawa, S. and Shioiri, T. J. Synth. Org. Chem. Jpn. 1981, 39, 741; b) Hogg, D. R. "Comprehensive Organic Chemistry," vol. 3, Jones, D. N. Ed., Pergamon Press, Oxford, 1979, pp. 302-307; c) Guy, R. G. "The Chemistry of Cyanates and Their Thio Derivatives," chap. 18, Patai, S. Ed., John Wiley & Sons, Chichester, 1977, pp. 819-886; d) Knoke, D., Kottke, K. and Pohloudek-Fabini, R. Pharmazie, 1977, 32, 195; e) Bacon, R. G. R. "Organic Sulfur Compounds," chap. 27, Kharasch, N. Ed., Pergamon Press, New York, 1961, vol. 1, pp. 306-325; f) Bögemann, M., Peterson, S., Schultz, O-E. and Söll, H. "Methoden der Organischen Chemie (Houben-Weyl)," bd. 9, Müller, E. Ed., Georg Thieme Verlag, Stuttgart, 1955, pp. 856-867.
2. For general survey of thiocyanates, see: a) Harusawa, S. and Shioiri, T. J. Synth. Org. Chem. Jpn. 1981, 39, 741; b) Hogg, D. R. "Comprehensive Organic Chemistry," vol. 3, Jones, D. N. Ed., Pergamon Press, Oxford, 1979, pp. 302-307; c) Guy, R. G. "The Chemistry of Cyanates and Their Thio Derivatives," chap. 18, Patai, S. Ed., John Wiley & Sons, Chichester, 1977, pp. 819-886; d) Knoke, D., Kottke, K. and Pohloudek-Fabini, R. Pharmazie, 1977, 32, 195; e) Bacon, R. G. R. "Organic Sulfur Compounds," chap. 27, Kharasch, N. Ed., Pergamon Press, New York, 1961, vol. 1, pp. 306-325; f) Bögemann, M., Peterson, S., Schultz, O-E. and Söll, H. "Methoden der Organischen Chemie (Houben-Weyl)," bd. 9, Müller, E. Ed., Georg Thieme Verlag, Stuttgart, 1955, pp. 856-867.
3. For general survey of thiocyanates, see: a) Harusawa, S. and Shioiri, T. J. Synth. Org. Chem. Jpn. 1981, 39, 741; b) Hogg, D. R. "Comprehensive Organic Chemistry," vol. 3, Jones, D. N. Ed., Pergamon Press, Oxford, 1979, pp. 302-307; c) Guy, R. G. "The Chemistry of Cyanates and Their Thio Derivatives," chap. 18, Patai, S. Ed., John Wiley & Sons, Chichester, 1977, pp. 819-886; d) Knoke, D., Kottke, K. and Pohloudek-Fabini, R. Pharmazie, 1977, 32, 195; e) Bacon, R. G. R. "Organic Sulfur Compounds," chap. 27, Kharasch, N. Ed., Pergamon Press, New York, 1961, vol. 1, pp. 306-325; f) Bögemann, M., Peterson, S., Schultz, O-E. and Söll, H. "Methoden der Organischen Chemie (Houben-Weyl)," bd. 9, Müller, E. Ed., Georg Thieme Verlag, Stuttgart, 1955, pp. 856-867.
4. For general survey of thiocyanates, see: a) Harusawa, S. and Shioiri, T. J. Synth. Org. Chem. Jpn. 1981, 39, 741; b) Hogg, D. R. "Comprehensive Organic Chemistry," vol. 3, Jones, D. N. Ed., Pergamon Press, Oxford, 1979, pp. 302-307; c) Guy, R. G. "The Chemistry of Cyanates and Their Thio Derivatives," chap. 18, Patai, S. Ed., John Wiley & Sons, Chichester, 1977, pp. 819-886; d) Knoke, D., Kottke, K. and Pohloudek-Fabini, R. Pharmazie, 1977, 32, 195; e) Bacon, R. G. R. "Organic Sulfur Compounds," chap. 27, Kharasch, N. Ed., Pergamon Press, New York, 1961, vol. 1, pp. 306-325; f) Bögemann, M., Peterson, S., Schultz, O-E. and Söll, H. "Methoden der Organischen Chemie (Houben-Weyl)," bd. 9, Müller, E. Ed., Georg Thieme Verlag, Stuttgart, 1955, pp. 856-867.
5. For general survey of thiocyanates, see: a) Harusawa, S. and Shioiri, T. J. Synth. Org. Chem. Jpn. 1981, 39, 741; b) Hogg, D. R. "Comprehensive Organic Chemistry," vol. 3, Jones, D. N. Ed., Pergamon Press, Oxford, 1979, pp. 302-307; c) Guy, R. G. "The Chemistry of Cyanates and Their Thio Derivatives," chap. 18, Patai, S. Ed., John Wiley & Sons, Chichester, 1977, pp. 819-886; d) Knoke, D., Kottke, K. and Pohloudek-Fabini, R. Pharmazie, 1977, 32, 195; e) Bacon, R. G. R. "Organic Sulfur Compounds," chap. 27, Kharasch, N. Ed., Pergamon Press, New York, 1961, vol. 1, pp. 306-325; f) Bögemann, M., Peterson, S., Schultz, O-E. and Söll, H. "Methoden der Organischen Chemie (Houben-Weyl)," bd. 9, Müller, E. Ed., Georg Thieme Verlag, Stuttgart, 1955, pp. 856-867.
6. For general survey of thiocyanates, see: a) Harusawa, S. and Shioiri, T. J. Synth. Org. Chem. Jpn. 1981, 39, 741; b) Hogg, D. R. "Comprehensive Organic Chemistry," vol. 3, Jones, D. N. Ed., Pergamon Press, Oxford, 1979, pp. 302-307; c) Guy, R. G. "The Chemistry of Cyanates and Their Thio Derivatives," chap. 18, Patai, S. Ed., John Wiley & Sons, Chichester, 1977, pp. 819-886; d) Knoke, D., Kottke, K. and Pohloudek-Fabini, R. Pharmazie, 1977, 32, 195; e) Bacon, R. G. R. "Organic Sulfur Compounds," chap. 27, Kharasch, N. Ed., Pergamon Press, New York, 1961, vol. 1, pp. 306-325; f) Bögemann, M., Peterson, S., Schultz, O-E. and Söll, H. "Methoden der Organischen Chemie (Houben-Weyl)," bd. 9, Müller, E. Ed., Georg Thieme Verlag, Stuttgart, 1955, pp. 856-867.
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21. From disulfides: a) Kawamura, S., Nakabayashi, T., Abe, Y. and Horii, T. Annu. Rep. Radiat. Cent. Osaka Prefect. 1983, 24, 63; Chem. Abstr. 1985, 102, 5680f; b) Degani, Y. and Patchornik, A. J. Org. Chem. 1971, 36, 2727; see ref. 10 also.
22. From disulfides: a) Kawamura, S., Nakabayashi, T., Abe, Y. and Horii, T. Annu. Rep. Radiat. Cent. Osaka Prefect. 1983, 24, 63; Chem. Abstr. 1985, 102, 5680f; b) Degani, Y. and Patchornik, A. J. Org. Chem. 1971, 36, 2727; see ref. 10 also.
23. From sulfenyl thiocyanates: Friedrich, F. and Pohloudek-Fabini, R. Arch. Pharm. 1965, 298, 162.
24. From thiosulfates: Footner, H. B. and Smiles, S. J. Chem. Soc. 1926, 2887.
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26. From sulfinates: a) Kagabu, S., Sawahara, K., Maehara, M., Ichihashi, S. and Saito, K. Chem. Pharm. Bull. 1991, 39, 784; b) Harusawa, S. and Shioiri, T. Tetrahedron Lett. 1982, 23, 447.
27. From N-arylthio imides: a) Furukawa, M., Suda, T. and Hayashi, S. Chem. Pharm. Bull. 1976, 24, 1708; b) Furukawa, M., Suda, T. and Hayashi, S. Chem. Lett. 1974, 881.
28. From N-arylthio imides: a) Furukawa, M., Suda, T. and Hayashi, S. Chem. Pharm. Bull. 1976, 24, 1708; b) Furukawa, M., Suda, T. and Hayashi, S. Chem. Lett. 1974, 881.
29. From sulfonyl halides: Han, G. and Wen, H. Chin. Chem. Lett. 1991, 2, 843; Chem. Abstr. 1992, 116, 173664m; see ref. 15a also.
30. From sulfonyl halides: Han, G. and Wen, H. Chin. Chem. Lett. 1991, 2, 843; Chem. Abstr. 1992, 116, 173664m; see ref. 15a also.
31. a) Uemura, S., Uchida, S., Okano, M. and Ichikawa, K. Bull. Chem. Soc. Jpn. 1973, 46, 3254;
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