L-proline-promoted CuI-catalyzed C-S bond formation between aryl iodides and thiols

Synthetic Communications

Volumn 37, Issue 1, 2007, Pages 25-35

  Zhang, Hui ^a   Cao, Weiguo ^a,b   Ma, Dawei ^b  

^a SHANGHAI UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl sulfide; Copper iodide; Cross coupling; L proline

Indexed keywords

ALIPHATIC COMPOUND; AROMATIC COMPOUND; CARBON; COPPER DERIVATIVE; CUPRIC IODIDE; IODINE DERIVATIVE; LIGAND; PROLINE; SULFIDE; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION;

EID: 33846954787     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600977533     Document Type: Article

References (36)

1. (a) Liu, L.; Stelmach, J. E.; Natarajan, S. R.; Chen, M.-H.; Singh, S. B.; Schwartz, C. D.; Fitzgerald, C. E.; O'Keefe, S. J.; Zaller, D. M.; Schmata, D. M.; Doherty, J. B. SAR of 3,4-Dihydropyrido[3,2-d]pyrimidone p38 inhibitors. Bioorg. Med. Chem. Lett. 2003, 13, 3979-3982;
2. (b) Arguello, J. E.; Schmidt, L. C.; Penenory, A. B. "One-pot" two-step synthesis of aryl sulfur compounds by photoinduced reactions of thiourea anion with aryl halides. Org. Lett. 2003, 5, 4133-4136;
3. (c) Zhang, X.-M.; Ma, M.; Wang, J.-B. Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from carbenoids and allenic 2-methylphenyl sulfide. Chin. J. Chem. 2003, 21, 878-882;
4. (d) Yao, H.; Richardson, D. E. Bicarbonate surfoxidants: Micellar oxidations of aryl sulfides with bicarbonate-activated hydrogen peroxide. J. Am. Chem. Soc. 2003, 125, 6211-6221;
5. (e) Savarin, C.; Srogl, J.; Liebeskind, L. S. A mild, nonbasic synthesis of thioethers: The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides. Org. Lett. 2002, 4, 4309-4312;
6. (f ) Nose, M.; Suzuki, H. Convient one-pot procedure for converting aryl sulfides to nitroaryl sulfones. Synthesis 2002, 1065-1071;
7. (g) Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen, B.; Marsh, K. C.; Okasinski, G. F.; von Geldern, T. W.; Ormes, M.; Fowler, K.; Gallatin, M. Discovery of novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction, 1: Identification of an additional binding pocket based on an anilino diaryl sulfide lead. J. Med. Chem. 2000, 43, 4025-4040.
8. Kondo, T.; Mitsudo, T. Metal-catalyzed carbon-sulfur bond formation. Chem. Rev. 2000, 100, 3205-3220.
9. (a) Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols. J. Am. Chem. Soc. 2006, 128, 2180-2181, ASAP article;
10. (b) Itoh, T.; Mase, T. A general palladium-catalyzed coupling of aryl bromides/triflates and thiols. Org. Lett. 2004, 6, 4587-4590;
11. (c) Murata, M.; Buchwald, S. L. A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines. Tetrahedron 2004, 60, 7397-7403;
12. (d) Moreau, X.; Campagne, J.-M. Palladium catalyzed thiol cross-coupling of cysteine derivatives with aryl and alkenyl halides. J. Organomet. Chem. 2003, 687, 322;
13. (e) Wolf, C.; Lerebours, R. Use of highly active palladium-phosphinous acid catalysts in Stille, Heck, amination, and thiation reactions of chloroquinolines. J. Org. Chem. 2003, 68, 7077;
14. (f) Baskin, J. M.; Wang, Z. An efficient copper catalyst for the formation of sulfones from sulfinic acid salts and aryl iodides. Org. Lett. 2002, 4, 4423;
15. (g) Li, G. Highly active, air-stable palladium catalysts for the C-C and C-S bond-forming reactions of vinyl and aryl chlorides: Use of commercially available [(t-Bu)(2)P(OH)](2)PdCl(2), [(t-Bu)(2)P(OH)PdCl(2)](2), and [[(t-Bu)(2)PO. . .H. . .OP(t-Bu)(2)]PdCl] (2) as catalysts. J. Org. Chem. 2002, 67, 3643;
16. (h) Schopfer, U.; Schlapbach, A. A general palladium-catalyzed synthesis of aromatic and heteroaromatic thioethers. Tetrahedron 2001, 57, 3069.
17. (a) Kunz, K.; Scholz, U.; Ganzer, D. Renaissance of Ullmann and Goldberg reactions - progress in copper catalyzed C-N-, C-O- and C-S-coupling. Synlett 2003, 2428-2439;
18. (b) Ley, S. V.; Thomas, A. W. Morden synthetic methods for copper-mediated C (aryl)-O, C (aryl)-N, and C(aryl)-S bond formation. Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
19. (c) Deng, W.; Liu, L.; Guo, Q.-X. Recent progress in copper-catalyzed cross-coupling reactions. Chin. J. Org. Chem. 2004, 24, 150.
20. Lindery, J. Copper assisted nucleophilic substitution of aryl halogen. Tetrahedron 1984, 40, 1433-1456.
21. Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. A general method for the formation of aryl-sulfur bonds using copper (I) catalysts. Org. Lett. 2002, 4, 2803-2806.
22. Kong, F. Y.; Buchwald, S. L. A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols. Org. Lett. 2002, 4, 3517-3520.
23. Wu, Y.-J.; He, H. Copper-catalyzed cross-coupling of aryl halides and thiols using microwave heating. Synlett 2003, 1789.
24. Naus, P.; Leseticky, L.; Smrcek, S.; Tislerova, I.; Sticha, M. Copper-assisted arylation of 1-thiosugars: Efficient route to triazene substituted arylthioglycosides. Synlett 2003, 2117.
25. (a) Ma, D.; Cai, Q. N,N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides. Org. Lett. 2003, 5, 3799-3802;
26. (b) Ma, D.; Cai, Q.; Zhang, H. Mild method for Ullmann coupling reaction of amines and aryl halides. Org. Lett. 2003, 5, 2453-2455;
27. (c) Ma, D.; Cai, Q. L-Proline promoted Ullmann-type coupling reactions of aryl iodides with indoles, pyrroles, imidazoles or pyrazoles. Synlett 2004, 128-130;
28. (d) Zhu, W.; Ma, D. Synthesis of aryl azides and vinyl azides via proline promoted CuI-catalyzed coupling reactions. Chem. Commun. 2004, 888-889;
29. (e) Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions. Synthesis 2005, 496-499;
30. (f ) Zhang, H.; Cai, Q.; ;Ma, D. Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles. J. Org. Chem. 2005, 70, 5164-5173.
31. Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands. Synlett 2004, 1254-1258.
32. Bordwell, F. G. Equilibrium acidities in dimethyl sulfoxide solution. Acc. Chem. Res. 1988, 21, 456-463.
33. Hambly, A. N.; O'Grady, B. V. Hydrogen bonding in organic compounds, IX: Intramolecular reactions between the primary amino group and amino, nitro, sulfide, and sulfone groups in aromatic compounds. Aust. J. Chem. 1964, 17, 860-876.
34. Cutler, R. R.; Stenger, R. J.; Suter, C. M. New antibacterial agents: 2-Acylamino-1-(4-hydrocarbonyl sulfonylphenyl)-1,3-propanediols and related compounds. J. Am. Chem. Soc. 1952, 74, 5475-5481.
35. Franke, A.; Mattern, G.; Traber, W. Synthetic juvenile hormones, 1: The p-substituted methylcinnamic acid derivatives. Helv. Chim. Acta 1975, 58, 268-278.
36. Du Pont de Nemours. US patent 2763692, 1955.