Nonbasic, room temperature, palladium-catalyzed coupling of aryl and alkenyl iodides with boronic acids mediated by copper(I) thiophene-2-carboxylate (CuTC)

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2149-2151

  Savarin, Cecile ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORONIC ACID DERIVATIVE; COPPER; IODINATED HYDROCARBON; PALLADIUM; THIOPHENE 2 CARBOXYLATE; THIOPHENE DERIVATIVE; THIOPHENE-2-CARBOXYLATE;

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

ALKENES; BORONIC ACIDS; CATALYSIS; COPPER; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; PALLADIUM; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 0035850279     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010060p     Document Type: Article

References (14)

1. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
2. (b) Suzuki, A. Pure Appl. Chem. 1994, 66, 2, 213-222.
3. (c) Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221-230.
4. (d) Li, Y.; Hong, X. M.; Collard, D. M.; El-Sayed, M. A. Org. Lett. 2000, 2 (15), 2385-2388.
5. (a) Littke, A.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
6. (b) Bei, X.; Turner, H. W.; Weinberrg, W.; Guram, A. S. J. Org. Chem. 1999, 64, 6797-6803.
7. Srogl, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2000, 122 (45), 11260-11261.
8. Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3 (1), 91-93.
9. 1 carboxylate-mediated couplings of boronic acids with heteroaryl thioethers and thioimidates will be disclosed shortly.
10. The pH of distilled water is unchanged in the presence of a CuTC slurry.
11. Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205-9219.
12. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312-2313.
13. Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342-5349.
14. 4(81 mg, 0.7 mmol, 3%), and CuTC (476 mg, 2.5 mmol, 1.1 equiv). The reaction was stirred for 3 h at room temperature. After purification by radial chromatography (hexanes), 1 (348 mg, 2.1 mmol, 90%) was obtained as a white solid.