Polymethylhydrosiloxane (PMHS) as an additive in Sonogashira reactions

Synlett

Volumn , Issue 4, 2003, Pages 537-541

  Gallagher, William P ^a   Maleczka Jr , Robert E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Alkynes; Copper; Cross coupling; Enynes; Palladium; Sonogashira reaction

Indexed keywords

CESIUM; FLUORINE; POLYMETHYLHYDROSILOXANE; SILICON DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; PURIFICATION; REACTION TIME; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE;

EID: 0037237176     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37522     Document Type: Article

References (43)

1. Maleczka, R. E. Jr.; Gallagher, W. P. Org. Lett. 2001, 3, 4173; and references cited.
2. For reviews see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chap. 5. (c) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998, Chap. 10. (d) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127. (e) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 2.4.
3. For reviews see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chap. 5. (c) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998, Chap. 10. (d) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127. (e) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 2.4.
4. For reviews see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chap. 5. (c) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998, Chap. 10. (d) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127. (e) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 2.4.
5. For reviews see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chap. 5. (c) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998, Chap. 10. (d) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127. (e) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 2.4.
6. For reviews see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chap. 5. (c) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998, Chap. 10. (d) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127. (e) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 2.4.
7. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
8. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
9. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
10. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
11. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
12. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
13. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
14. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
15. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
16. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
17. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
18. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
19. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
20. For recent advances see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (b) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756. (c) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118. (d) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed. 2002, 41, 4500. (e) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (f) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815. (g) Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2000, 3, 4107. (h) Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165. (i) Nishihara, Y.; Ando, J.-i.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. L.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780. (m) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (n) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233.
21. 3N.
22. For other examples of amine free Sonogashira-type reactions see (a) Alonso, D. A.; Nájera, C.; Pacheco, C. Tetrahedron Lett. 2002, 43, 9365. (b) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649.
23. For other examples of amine free Sonogashira-type reactions see (a) Alonso, D. A.; Nájera, C.; Pacheco, C. Tetrahedron Lett. 2002, 43, 9365. (b) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649.
24. (a) Lawrence, N. J.; Drew, M. D.; Bushell, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 3381.
25. (b) Lipowitz, J.; Bowman, S. A. Aldrichimica Acta 1973, 6, 1.
26. (c) Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis, Vol. 4; Wiley: New York, 1974, 393.
27. 2 to work efficiently. For other examples of CuTC in coupling reactions see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260. (c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
28. 2 to work efficiently. For other examples of CuTC in coupling reactions see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260. (c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
29. 2 to work efficiently. For other examples of CuTC in coupling reactions see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260. (c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
30. Couplings of 1 and 2 with 1.0 or 1.5 equiv of CuTC were lower yielding (44-68%).
31. (a) Rottländer, M.; Knochel, P. J. Org. Chem. 1998, 63, 203.
32. (b) For a review of the preparation of alkenyl triflates see: Lyapkalo, I. M.; Webel, M.; Reißig, H.-U. Eur. J. Org. Chem. 2002, 1015.
33. 4), filtered and concentrated. The resulting residue was purified by column chromatography (silica gel; hexane/EtOAc 90:10) to afford 1-(4-phenylethynyl-phenyl)-ethanone(5) (212 mg, 96%) as a light yellow solid (mp 95 °C). For spectroscopic data and a prior preparation see the following: Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017.
34. CuCl could also be used, but the reaction yields tended to be slightly lower.
35. 10) was followed except that 2 equiv of CuTC were used and the solvent was THF/NMP (1:1, 15 mL at 1.0 mmol scale).
36. Adding the alkyne, CsF, and PMHS at once caused rapid foaming that made monitoring by ReactIR™ difficult.
37. Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020.
38. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280.
39. 3 or TBAF. See:
40. 3 or TBAF. See: (a) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039. (b) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641. (c) Bertus, P.; Halbes, U.; Pale, P. Eur. J. Org. Chem. 2001, 4391.
41. 3 or TBAF. See: (a) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039. (b) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641. (c) Bertus, P.; Halbes, U.; Pale, P. Eur. J. Org. Chem. 2001, 4391.
42. 3 or TBAF. See: (a) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039. (b) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641. (c) Bertus, P.; Halbes, U.; Pale, P. Eur. J. Org. Chem. 2001, 4391.
43. Edelson, B. S.; Stoltz, B. M.; Corey, E. J. Tetrahedron Lett. 1999, 40, 6729.