Substituted alkyne synthesis under nonbasic conditions: Copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling

Organic Letters

Volumn 3, Issue 1, 2001, Pages 91-93

  Savarin, Cecile ^a   Srogl, Jiri ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BORONIC ACID DERIVATIVE; COPPER; PALLADIUM; SALICYLIC ACID DERIVATIVE; SALICYLIC ACID METHYL ESTER; SULFUR DERIVATIVE; THIOPHENE 2 CARBOXYLATE; THIOPHENE DERIVATIVE; THIOPHENE-2-CARBOXYLATE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKYNES; BORONIC ACIDS; CATALYSIS; COPPER; MOLECULAR STRUCTURE; PALLADIUM; SALICYLATES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS; THIOPHENES;

EID: 0035843313     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006807d     Document Type: Article

References (20)

1. Patai, S. The Chemistry of the Carbon-Carbon Triple Bond; Wiley: New York, 1978.
2. Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: New York, 1988.
3. (a) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998; p 198.
4. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
5. (c) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 5, 549-550.
6. (d) Thorand, S.; Krause, N. J. Org. Chem. 1958, 23, 8551-8553.
7. (a) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437-3440.
8. (b) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
9. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114 (23), 8869-8885.
10. Busi, E.; Capozzi, G.; Menichetti, S.; Nativi, C. Synthesis 1992, 7, 643-645.
11. (a) Takeda, H.; Shimada, S.; Ohnishi, S.; Nakanishi, F.; Matsuda, H. Tetrahedron Lett. 1998, 39, 3701-3704.
12. (b) Braga, A. L.; Silveira, C. C.; Reckziegle, A.; Menezes, P. H Tetrahedron Lett. 1993, 34, 8041-8042.
13. (c) Stang, P. J.; Zhankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571-4576.
14. (d) Tanaka, K.; Shiraishi, S.; Nakai, T.; Ishikawa, N. Tetrahedron Lett. 1978, 34, 3103-3106.
15. Other recent copper carboxylate-mediated reactions: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312-2313.
16. Other recent copper carboxylate-mediated reactions: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312-2313.
17. Liebeskind, L. S. Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261.
18. Other references to C-S oxidative addition are found within Kuniyasu, H.; Ohtaka, A.; Nakazono, T.; Kinomoto, M.; Kurosawa, H. J. Am. Chem. Soc. 2000, 122, 2375-2376.
19. 4 (502 mg, 0.43 mmol, 1.0 equiv) in dry and degassed benzene (11 mL), at room temperature, in the dark, under argon. After 10 h, pentane (60 mL), was added and an orange solid precipitated. After filtration of the solid, the palladium complex 19 (230 mg, 0.27 mmol, 63%) was obtained as a lightly orange solid.
20. 2 as eluent), 18 (37 mg, 0.09 mmol, 81%) was obtained as white crystals. Full details are contained in the Supporting Information.