RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2013; 45(16): 2323-2327
DOI: 10.1055/s-0033-1339186
DOI: 10.1055/s-0033-1339186
paper
Copper(I) Iodide Catalyzed Synthesis of Thiophosphates by Coupling of H-Phosphonates with Benzenethiols
Weitere Informationen
Publikationsverlauf
Received: 27. März 2013
Accepted after revision: 15. Mai 2013
Publikationsdatum:
25. Juni 2013 (online)
Abstract
A simple, efficient, and new method has been developed for the preparation of thiophosphates from benzenethiols. The method involves copper(I) iodide catalyzed coupling of thiols with H-phosphonates in the presence of triethylamine. The reaction proceeds effectively to afford the corresponding thiophosphates in moderate to good yields via an aerobic dehydrogenative coupling of H-phosphonates with benzenethiols. This method is easy, rapid, and good-yielding for the synthesis of thiophosphates from benzenethiols.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Toy A, Walsh EN. Phosphorus Chemistry in Everyday Living . 2nd ed. American Chemical Society; Washington DC: 1987: Chap. 18-20
- 1b Quin LD. A Guide to Organophosphorus Chemistry. Wiley; New York: 2000
- 2a Gallo MA, Lawryk NJ. Organic Phosphorus Pesticides. The Handbook of Pesticide Toxicology. Academic Press; San Diego: 1991
- 2b Chernier PJ. Survey of Industrial Chemistry . 2nd ed. Wiley-VCH; New York: 1992: 389-417
- 3 Hassall KA. The Biochemistry and Uses of Pesticides . 2nd ed. VCH; Weinheim: 1990: 269-275
- 4a Fukuoka M, Shuto S, Minakawa N, Ueno Y, Matsuda A. J. Org. Chem. 2000; 65: 5238
- 4b Fukuoka M, Shuto S, Minakawa N, Ueno Y, Matsuda A. Tetrahedron Lett. 1999; 40: 5361
- 4c Huang L.-J, Zhao Y.-Y, Yuan L, Min J.-M, Zhang L.-H. J. Med. Chem. 2002; 45: 5340
- 4d Marinozzi M, Fulco MC, Rizzo R, Pellicciari R. Synlett 2004; 1027
- 4e Glass RS, Singh WP, Jung W, Veres Z, Scholz TD, Stadtman T. Biochemistry 1993; 53: 15085
- 5 Han L.-B, Tanaka M. Chem. Lett. 1999; 863
- 6a Kaboudin A, Emadi S, Hadizadeh A. Bioorg. Chem. 2009; 37: 101
- 6b Gabelt BT, Hennes EA, Seeman JL, Tian B, Kaufman PL. Invest. Ophthalmol. Vis. Sci. 2004; 45: 2732
- 6c Fraietta JA, Mueller YM, Do DH, Holmes VM, Howett MK, Lewis MG, Boesteanu AC, Alkan SS, Katsikis PD. Antimicrob. Agent Chemother. 2010; 54: 4064
- 7 Yoshido M, Maeda T, Sugiyama H. Japanese Patent C1.16 C 92, 1967 ; Chem. Abstr. 1967, 66, 115455.
- 8a Folkin AV, Kolomiets AF, Iznoskova MG. Izv. Akad. Nauk SSSR, Ser. Khim. 1974; 2837 ; Chem. Abstr. 1975, 82, 97323
- 8b Schrader G. U.S. Patent 2 597 534, 1953 ; Chem. Abstr. 1953, 47, 4357h.
- 9 Michalski J, Modro T, Wieczorkowski J. J. Chem. Soc. 1960; 1665
- 10a Michalski J, Wasiak J. J. Chem. Soc. 1962; 5056
- 10b Michalski J, Wieczorkowski J, Wasiak J, Pliszka B. Rocz. Chem. 1959; 33: 247 ; Chem. Abstr. 1959, 53, 17884
- 10c Harvey RG, Jacobson HI, Jensen EV. J. Am. Chem. Soc. 1963; 85: 1618
- 10d Gao Y.-X, Tang G, Cao Y, Zhao Y.-F. Synthesis 2009; 1081
- 11a Sato Z, Takagi K, Imamiya Y, Shimizu F, Kusano S. Ger. Offen. 2 601 532 (C1.CO7F9/17), 1976 ; Chem. Abstr. 1976, 85, 123628.
- 11b Hashimoto T, Ohkubo T. Japanese Patent 77 10 868 (C1.CO7F9/06), 1977 ; Chem. Abstr. 1977, 87, 134503.
- 11c Schrader G, Lorenz W. U.S. Patent 2 862 017, 1958 ; Chem. Abstr. 1960, 54, 1438a.
- 11d Farbenfabriken Bayer Akt.-Ges British Patent 814332, 1959 ; Chem. Abstr. 1960, 54, 17330c.
- 11e Kabachnik MI, Mastrykova TA. Zh. Obshch. Khim. 1955; 25: 1924 ; Chem. Abstr. 1956, 50, 8499d
- 11f Kaboudin B. Tetrahedron Lett. 2002; 43: 8713
- 11g Kaboudin B, Farjadian F. Beilstein J. Org. Chem. 2006; 2: 4
- 11h Kaboudin B, Norouzi H. Tetrahedron Lett. 2004; 45: 1283
- 11i Kaboudin B, Emadi S, Hadizadeh A. Bioorg. Chem. 2009; 37: 101
- 12a Schrader G, Lorens W. German Patent 817 057 (C1.45l,3ol), 1951 ; Chem. Abstr. 1954, 48, 6643d.
- 12b Sallmann R. Swiss Patent 324980, 1957 ; Chem. Abstr. 1958, 52, 14960a.
- 13 Takamizawa A, Sato Y, Tanaka S. Yakugaku Zasshi 1965; 298 , Chem. Abstr. 1965, 63, 9940h
- 14a Kaboudin B, Abedi Y, Yokomatsu T. Eur. J. Org. Chem. 2011; 6656
- 14b Kaboudin B, Abedi Y, Yokomatsu T. Org. Biomol. Chem. 2012; 10: 4543
- 14c Kaboudin B. Tetrahedron Lett. 2003; 44: 1051
- 14d Kaboudin B, Karimi M. Bioorg. Med. Chem. Lett. 2006; 16: 5324
- 14e Kaboudin B, Moradi K. Synthesis 2006; 2339
- 14f Kaboudin B, Jafari E. Synthesis 2006; 3063
- 14g Kaboudin B, Elahamifar D. Synthesis 2006; 224
- 14h Kaboudin B, Sorbiun M. Tetrahedron Lett. 2007; 48: 9015
- 14i Kaboudin B, Saadati F. Tetrahedron Lett. 2007; 48: 2829
- 14j Kaboudin B, Jafari E. Synthesis 2008; 2683
- 14k Kaboudin B, Haghighat H, Yokomatsu T. Tetrahedron: Asymmetry 2008; 19: 862
- 14l Kaboudin B, Saadati F. Tetrahedron Lett. 2009; 50: 1450
- 14m Kaboudin B, Fallahi M. Tetrahedron Lett. 2011; 52: 4346
- 15 Zhou Y, Yin S, Gao Y, Zhao Y, Goto M, Han L.-B. Angew. Chem. Int. Ed. 2010; 49: 6852
- 16 Murdock LL, Hopkins TL. J. Org. Chem. 1968; 33: 907
- 17 Hoffmann FW, Moore TR, Kagan B. J. Am. Chem. Soc. 1956; 78: 6413
- 18 Nilsson J, Kraszewski A, Stawinski J. J. Chem. Soc., Perkin Trans. 2 2001; 2263
- 19 Han X, Wu J. Org. Lett. 2010; 12: 5780
For example: