Sonogashira cross-couplings of ynamides. Syntheses of urethane- and sulfonamide-terminated conjugated phenylacetylenic systems

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2209-2212

  Tracey, Michael R ^a   Zhang, Yanshi ^a   Frederick, Michael O ^a   Mulder, Jason A ^a   Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AMIDE; IODIDE; SULFONAMIDE; URETHAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; HALOGENATION; REACTION ANALYSIS; SONOGASHIRA REACTION; SYNTHESIS;

EID: 3142699919     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0493251     Document Type: Article

References (59)

1. For reviews on ynamides, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
2. For reviews on ynamides, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. (b) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
3. For the first preparations of ynamides, see: (c) Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917.
4. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
5. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
6. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
7. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
8. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
9. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
10. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
11. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
12. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
13. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
14. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
15. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
16. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
17. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
18. For recent efforts in synthesis and applications of ynamides, see: (a) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. (c) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (d) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (e) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (f) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (g) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (h) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (i) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (j) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (k) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637. (l) Minière, S.; Cintrat. J.-C. Synthesis 2001, 705. (m) Minière, S.; Cintrat. J.-C. J. Org. Chem. 2001, 66, 7385. (n) Hoffmann, R. W.; Brückner, D. New. J. Chem. 2001, 25, 369. (o) For citations appearing before 2001, see ref la,b.
19. For our recent applications of ynamides, see: (a) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (e) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383. (f) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
20. For our recent applications of ynamides, see: (a) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (e) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383. (f) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
21. For our recent applications of ynamides, see: (a) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (e) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383. (f) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
22. For our recent applications of ynamides, see: (a) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (e) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383. (f) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
23. For our recent applications of ynamides, see: (a) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (e) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383. (f) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
24. For our recent applications of ynamides, see: (a) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (d) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (e) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383. (f) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
25. For our syntheses of ynamides using copper-catalyzed amidations of alkynyl bromides, see: (a) Zhang, Y.; Hsung R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151. (b) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
26. For our syntheses of ynamides using copper-catalyzed amidations of alkynyl bromides, see: (a) Zhang, Y.; Hsung R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151. (b) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
27. For two related accounts involving synthesis of ynamides using copper metal, see: (a) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011. (b) Also see ref 2b for CuI-catalyzed N-alkynylations reported by Urabe and Sato.
28. For two related accounts involving synthesis of ynamides using copper metal, see: (a) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011. (b) Also see ref 2b for CuI-catalyzed N-alkynylations reported by Urabe and Sato.
29. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 76, 4467,
30. For reviews on Heck couplings, see: (b) Hegedus, L. S. Tetrahedron 1984, 40, 2415.
31. For reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002; Vol I, p 7. (c) Sonogashira, K. Cross-coupling reactions to sp carbon atoms. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCh: New York, 1998; pp 203-229.
32. For reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002; Vol I, p 7. (c) Sonogashira, K. Cross-coupling reactions to sp carbon atoms. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCh: New York, 1998; pp 203-229.
33. For reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002; Vol I, p 7. (c) Sonogashira, K. Cross-coupling reactions to sp carbon atoms. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCh: New York, 1998; pp 203-229.
34. During our pursuit of Sonogashira couplings, Saá reported an alternative Negishi coupling of sulfonyl ynamides and also documented the lack of feasibility in related Sonogashira coupling. See: Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783.
35. For reviews, see: (a) Ahmed, H. J. Vac. Sci. Technol, B 1997, 15, 2101. (b) Petty, M. C.; Bryce, M. R.; Bloor, D. Introduction to Molecular Electronics; Oxford University Press: New York, 1995. (c) Molecular Electronics and Molecular Electronic Devices; Sienicki, K., Ed.; CRC Press: Boca Raton, 1992; Vols. I-III. (d) Mirkin, C. A.; Ratner, M. A. Molecular electronics. Annu. Rev. Phys. Chem. 1992, 43, 719.
36. For reviews, see: (a) Ahmed, H. J. Vac. Sci. Technol, B 1997, 15, 2101. (b) Petty, M. C.; Bryce, M. R.; Bloor, D. Introduction to Molecular Electronics; Oxford University Press: New York, 1995. (c) Molecular Electronics and Molecular Electronic Devices; Sienicki, K., Ed.; CRC Press: Boca Raton, 1992; Vols. I-III. (d) Mirkin, C. A.; Ratner, M. A. Molecular electronics. Annu. Rev. Phys. Chem. 1992, 43, 719.
37. For reviews, see: (a) Ahmed, H. J. Vac. Sci. Technol, B 1997, 15, 2101. (b) Petty, M. C.; Bryce, M. R.; Bloor, D. Introduction to Molecular Electronics; Oxford University Press: New York, 1995. (c) Molecular Electronics and Molecular Electronic Devices; Sienicki, K., Ed.; CRC Press: Boca Raton, 1992; Vols. I-III. (d) Mirkin, C. A.; Ratner, M. A. Molecular electronics. Annu. Rev. Phys. Chem. 1992, 43, 719.
38. For reviews, see: (a) Ahmed, H. J. Vac. Sci. Technol, B 1997, 15, 2101. (b) Petty, M. C.; Bryce, M. R.; Bloor, D. Introduction to Molecular Electronics; Oxford University Press: New York, 1995. (c) Molecular Electronics and Molecular Electronic Devices; Sienicki, K., Ed.; CRC Press: Boca Raton, 1992; Vols. I-III. (d) Mirkin, C. A.; Ratner, M. A. Molecular electronics. Annu. Rev. Phys. Chem. 1992, 43, 719.
39. Also see: (a) Wada, Y. Surf. Sci. 1997, 386, 265. (b) Reimers, J. R.; Lu, T. X.; Crossley, M. J.; Hush, N. S. Nanotechnology 1996, 7, 424. (c) Conjugated Conducting Polymers; Springer Series in Solid-State Sciences, no. 102; Kiess H., Ed.; Springer-Verlag: Berlin, 1992.
40. Also see: (a) Wada, Y. Surf. Sci. 1997, 386, 265. (b) Reimers, J. R.; Lu, T. X.; Crossley, M. J.; Hush, N. S. Nanotechnology 1996, 7, 424. (c) Conjugated Conducting Polymers; Springer Series in Solid-State Sciences, no. 102; Kiess H., Ed.; Springer-Verlag: Berlin, 1992.
41. Also see: (a) Wada, Y. Surf. Sci. 1997, 386, 265. (b) Reimers, J. R.; Lu, T. X.; Crossley, M. J.; Hush, N. S. Nanotechnology 1996, 7, 424. (c) Conjugated Conducting Polymers; Springer Series in Solid-State Sciences, no. 102; Kiess H., Ed.; Springer-Verlag: Berlin, 1992.
42. (a) Dubois, L. H.; Nuzzo, R. G. Annu. Rev. Phys. Chem. 1992, 43, 437.
43. (b) Ulman, A. Chem. Rev. 1996, 96, 1533.
44. For some recent examples, see: (a) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. (b) Scherf, U.; Müllen, K. Synthesis 1992, 23. (c) Tour, J. M.; Jones, L., II; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. V.; Allara, D. L.; Parikh, A. N.; Atre, S. V. J. Am. Chem. Soc. 1995, 117, 9529.
45. For some recent examples, see: (a) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. (b) Scherf, U.; Müllen, K. Synthesis 1992, 23. (c) Tour, J. M.; Jones, L., II; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. V.; Allara, D. L.; Parikh, A. N.; Atre, S. V. J. Am. Chem. Soc. 1995, 117, 9529.
46. For some recent examples, see: (a) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. (b) Scherf, U.; Müllen, K. Synthesis 1992, 23. (c) Tour, J. M.; Jones, L., II; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. V.; Allara, D. L.; Parikh, A. N.; Atre, S. V. J. Am. Chem. Soc. 1995, 117, 9529.
47. (a) Dhirani, A.-A.; Zehner, W. R.; Hsung, R. P.; Guyot-Sionnest, P.; Sita, L. R. J. Am. Chem. Soc. 1996, 118, 3319.
48. (b) Sandra, S. B.; Dudek, S. P.; Hsung, R. P.; Sita, L. R.; Smalley, J. F.; Newton, M. D.; Feldberg, S. W.; Chidsey, C. E. D. J. Am. Chem. Soc. 1997, 119, 10563.
49. (c) Zehner, R. W.; Parsons, B. F.; Hsung, R. P.; Sita, L. R. Langmuir 1999, 15, 1121.
50. Relevant procedures for new compounds and their characterizations are in Supporting Information.
51. 4 (0.075 mmol, 5 mol %), 8 mL of TEA, and 4 mL of toluene. The solution was stirred at room temperature for 10 min, and 4.3 mg of CuI (1.5 mol %) was then added. After heating the reaction mixture at 60°C for 2 h, the mixture was diluted with EtOAc, filtered through Celite, and concentrated in vacuo. The resulting crude residue was purified by silica gel flash column chromatography (gradient 10% to 20% EtOAc in hexanes) to afford 473.0 mg (73% yield) of aryl ynamide 22.
52. (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
53. (b) For a review see: Cadiot, P.; Chodkiewicz, W. Coupling of acetylenes. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 597-647.
54. (c) For a recent review, see: Siemsen, P.; Livingston, R. C.; Diederich, F. Angew Chem., Int. Ed. 2000, 39, 2632.
55. The X-ray structure reveals that there is a slight bend along the acetylenic axis (N1-C10-C11-C12). More interestingly, the two planes of the o-methoxyphenyl ring and the oxazolidinone ring have an approximate dihedral angle of ∼79.9°, which is almost orthogonal as shown in the ChemDraw reproduction.
56. We are not certain as to why urethane-substituted ynamide 9 does not suffer to the same extent from the problem of homocoupling, with no need in controlling the addition order. However, from our available experiences now working with both urethane- and sulfonyl-substituted ynamides, the latter appears to be much more reactive than the former. Method B is also suitable for preparing these urethane-substituted ynamides
57. (a) Hsung, R. P.; Babcock, J. R.; Chidsey, C. E. D.; Sita, L. R. Tetrahedron Lett. 1995, 36, 4525.
58. (b) Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. Organometallics 1995, 14, 4808.
59. (c) Lavastre, O.; Ollivier, L.; Dixneuf, P. H.; Sibandhis, S. Tetrahedron 1996, 52, 5495.