Diazaphospholane as an efficient ligand for copper-catalyzed cross-coupling of thiols with aryl iodides

Letters in Organic Chemistry

Volumn 8, Issue 8, 2011, Pages 587-591

  Yang, Minghua ^a   Pei, Ji ^a   Yan, Guobing ^a   Zheng, Yunfa ^a  

^a LISHUI UNIVERSITY   (China)

Author keywords

Arylation; Copper; Cross coupling; Diazaphospholane; Thiols

Indexed keywords

EID: 80053007657     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811797249335     Document Type: Article

References (26)

1. Neilsen, S. F.; Neilsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. Novel potent ligands for the central nicotinic acetylcholine receptor: synthesis, receptor binding, and 3D-QSAR analysis. J. Med. Chem. 2000, 43, 2217.
2. Navarro, R.; Perrino, M. P.; Tardajos, M. G.; Reinecke, H. Phthalate plasticizers covalently bound to pvc: plasticization with suppressed migration. Macromolecules 2010, 43, 2377.
3. Sperotto, E.; Klink, G. P. M.; Vries, J. G.; Koten, G. Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols. J. Org. Chem., 2008, 73, 5625.
4. Duan, Z.; Ranjit, S.; Liu, X. One-pot synthesis of amine-substituted aryl sulfides and benzo[b]thiophene derivatives. Org. Lett. 2010, 12, 2430.
5. Deng, W.; Zou, Y.; Wang, Y.; Liu, L.; Guo, Q. CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligand. Synlett. 2004, 1254.
6. Ma, D.; Geng Q.; Zhang, H.; Jiang, Y. Assembly of substituted phenothiazines by a sequentially controlled CuI/L-prolinecatalyzed cascade C-S and C-N bond formation. Angew. Chem. Int. Ed. 2010, 49, 1291.
7. Zhang, H.; Cao, W.; Ma, D. L-proline-promoted CuI-catalyzed C-S bond formation between aryl iodides and thiols. Synth. Commun. 2007, 37, 25.
8. 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.
9. Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Copper-catalyzed synthesis of vinyl sulfides. Org. Lett. 2004, 6, 5005.
10. Haldón, E.; lvarez, E. Á.; Nicasio, M. C; Pérez, P. J. Dinuclear copper (I) complexes as precatalysts in Ullmann and Goldberg coupling reactions. Organometallics, 2009, 28, 3815.
11. Verma, A. K.; Singh, J.; Chaudhary, R. A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols. Tetrahedron Lett. 2007, 48, 7199.
12. Lv, X.; Bao W. A β-keto ester as a novel, efficient, and versatile ligand for copper (I)-catalyzed C-N, C-O, and C-S coupling reactions. J. Org. Chem. 2007, 72, 3863.
13. Kwong, 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.
14. Kabir, M. S.; Lorenz, M.; Linn, M. L. V.; Namjoshi, O. A.; Ara, S.; Cook, J. M. A very active Cu-catalytic system for the synthesis of aryl, heteroaryl, and vinyl sulfides. J. Org. Chem. 2010, 75, 3626.
15. Feng, Y.; Wang, H.; Sun, F.; Li, Y.; Fu, X.; Jin, K. A highly efficient and widely functional-group-tolerant catalyst system for copper (I)-catalyzed S-arylation of thiols with aryl halides. Tetrahedron 2009, 65, 9737.
16. Jogdand, N.; Shingate B. B.; Shingare, M. S. An efficient tris-(2-aminoethyl) amine-CuI-catalyzed thioetherification of thiols with aryl halides Tetrahedron Lett. 2009, 50, 6092.
17. Herrero, M. T.; San Martin, R.; Domínguez, E. Copper (I)-catalyzed S-arylation of thiols with activated aryl chlorides on water. Tetrahedron 2009, 65, 1500.
18. Hartwig, J. F. Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides. Acc. Chem. Res. 2008, 41, 1534.
19. Zhu, D.; Xu, L.; Wu, F.; Wan, B. A mild and efficient coppercatalyzed coupling of aryl iodides and thiols using an oximephosphine oxide ligand. Tetrahedron Lett. 2006, 47, 5781.
20. Palomo, C; Oiarbide, M.; López, R.; Gómez-Bengoa E. Phosphazene bases for the preparation of biaryl thioethers from aryl iodides and arenethiols. Tetrahedon Lett. 2000, 41, 1283.
21. Clark, T. P.; Landis, C. R.; Freed, S. L.; Klosin, J.; Abboud, K. A. Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by bis-3, 4-diazaphospholanes. Am. Chem. Soc. 2005, 127, 5040.
22. For a review on phospholane chemistry, see: Clark, T. P.; Landis, C. R. Recent developments in chiral phospholane chemistry. Tetrahedron: Asymmetry 2004, 15, 2123.
23. Yang, M.; Liu, F. An Ullmann coupling of aryl iodides and amines using an air-stable diazaphospholane ligand. J. Org. Chem. 2007, 72, 8969.
24. Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. Indiumcatalyzed C-S cross-coupling of aryl halides with thiols. J. Org. Chem. 2009, 74, 3189.
25. 2O/cationic 2, 2′-bipyridyl catalytic system for the coupling of aryl iodides with thiols in water under aerobic conditions. Green Chem. 2009, 11, 326.
26. Correa, A.; Carril, M.; Bolm, C. Iron-catalyzed S-arylation of thiols with aryl iodides. Angew. Chem. Int. Ed. 2008, 47, 2880.