"One-Pot" Two-Step Synthesis of Aryl Sulfur Compounds by Photoinduced Reactions of Thiourea Anion with Aryl Halides

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4133-4136

  Argüello, Juan E ^a   Schmidt, Luciana C ^a   Peñéñory, Alicia B ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFUR DERIVATIVE; THIOUREA;

ARTICLE; CHEMICAL REACTION; LIGHT; OXIDATION; PROTON TRANSPORT; SYNTHESIS;

EID: 2942743160     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035545n     Document Type: Article

References (18)

1. Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: Chischester, 1996.
2. March, J. Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 2001.
3. (a) Cu catalysis: Lindley, J. Tetrahedron 1984, 40, 1433-1456.
4. (b) Pd catalysis: Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-I.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
5. Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. Chem. Rev. 2003, 103, 71-167.
6. Rossi, R. A.; Palacios, S. M. J. Org. Chem. 1981, 46, 5300-5304.
7. Beugelmans, R.; Bois-Choussy, M.; Boudet, B. Tetrahedron 1983, 39, 4153-4161.
8. Combellas, C.; Dellerue, S.; Mathey, G.; Thiébault, A. Tetrahedron Lett. 1997, 38, 539-542.
9. Frolov, A. N.; Klokova, E. M.; El'tsov, A. V. J. Org. Chem. USSR (Engl. Transl.) 1981, 17, 1926-1935.
10. Representative Experimental Procedure. The reactions were carried out in a 10 mL three-necked Schlenk tube, equipped with nitrogen gas inlet and magnetic stirrer. The tube was dried under vacuum, filled with nitrogen, and then loaded with 10 mL of dried DMSO. 5.5 mmol of t-BuOK, 5 mmol of the thiourea, and 0.5 mmol of the aryl halide were added to the degassed solvent under nitrogen. After 3 h of irradiation with a medium-pressure Hg lamp emitting maximally at 350 nm, the reaction was quenched with addition of methyl iodide (6 equiv) and 30 mL of water, and then the mixture was extracted with methylene chloride (3 × 20 mL). The organic extract was washed twice with water and dried, and the products were quantified by GLC with the internal standard method.
11. -1 determined by Saveánt (Andrieux, C. P.; Savéant, J.-M.; Su, K. B. J. Phys. Chem. 1986, 90, 3815-3823) seems to be more adequate.
12. -1 determined by Saveánt (Andrieux, C. P.; Savéant, J.-M.; Su, K. B. J. Phys. Chem. 1986, 90, 3815-3823) seems to be more adequate.
13. Part of naphthalene is lost during the reaction and with the evaporation of the solvent.
14. 3. Toward 3-pyridyl radical (similar reactivity to naphthyl radical), benzene thiolate ion is 1 order of magnitude more reactive than ion 1 (ref 7).
15. Wuest, H. M.; Sakal, E. H. J. Am. Chem. Soc. 1951, 73, 1210-1216.
16. Hermann, C. K. F.; Sachdeva, Y. P.; Wolfe, J. F. J. Heterocycl. Chem. 1987, 24, 1061-1065.
17. Carver, D. R.; Komin, A. P.; Hubbard, J. S.; Wolfe, J. F. J. Org. Chem. 1981, 46, 294-299.
18. Petrillo, G.; Novi, M.; Garbarino, G.; Filiberti, M. Tetrahedron 1989, 45, 7411-7420.