A simple and convenient method for the synthesis of S-aryl phosphorothioates catalyzed by cesium hydroxide

Chinese Chemical Letters

Volumn 24, Issue 12, 2013, Pages 1103-1105

  Ouyang, Yue Jun ^a,b   Li, Yuan Yuan ^b   Li, Ning Bo ^b   Xu, Xin Hua ^b  

^a HUAIHUA UNIVERSITY   (China)

^b HUNAN UNIVERSITY   (China)

Author keywords

Cesium hydroxide; Diaryldisulfides; O,O Dialkyl S arylphosphorothioates

Indexed keywords

EID: 84888435208     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.06.020     Document Type: Article

References (23)

1. Z.J. He, W.B. Chen, and F.P. Ma The chlorination reaction of O-alkyl S-alkyl (aryl) thiophosphoric (nic) aicd derivatives with phosphorus Phosphorus Sulfur Silicon Relat. Elem. 142 1998 49 55
2. K.K. Adhikary, H.R. Barai, and H.W. Lee Kinetics and mechanism of the benzylaminolysis of O,O-dimethyl S-aryl phosphorothioates in dimethyl sulfoxide Bull. Korean Chem. Soc. 32 2011 3587 3591
3. S.B. Hong, and F.M. Raushel Metal-substrate interactions facilitate the catalytic activity of the bacterial phosphotriesterase Biochemistry 35 1996 10904 10912
4. A. Blaskó, C.A. Bunton, and A. Kumar Oxidative hydrolysis of phosphorus (V) esters of thiols by peroxymonosulfate ion. Reactions of peroxymonosulfate ion with phosphorus (V) esters of thiols J. Phys. Org. Chem. 10 1997 427 434
5. C.E. Müller, and H.J. Roth A new synthesis of thiophosphoric acid esters with a CSP bond Tetrahedron Lett. 31 1990 501 502
6. A. Gautier, G. Garipova, O. Dubert, H. Oulyadi, and S.R. Piettre Efficient and practical aerobic radical addition of thiophosphites to alkenes Tetrahedron Lett. 42 2001 5673 5676
7. T.F. Herpin, W.B. Motherwell, B.P. Roberts, S. Roland, and J.M. Weibel Free radical chain reactions for the preparation of novel anomeric carbohydrate difluoromethylene-phosphonates and -phosphonothioates Tetrahedron 53 1997 15085 15100
8. C. Lopin, G. Gouhier, A. Gautier, and S.R. Piettre Phosphonyl, phosphonothioyl, phosphonodithioyl, and phosphonotrithioyl radicals: generation and study of their addition onto alkenes J. Org. Chem. 68 2003 9916 9923
9. Q. Xu, C.G. Liang, and X. Huang Free radical reaction of dialkyl phosphites and organic dichalcogenides: a new facile and convenient preparation of arylselenophosphates Synth. Commun. 33 2003 2777 2785
10. G. Maryam, and S. Soheil A novel and efficient synthesis of alkyl thiocyanates from alkyl halides in water using phase transfer catalysts Chin. Chem. Lett. 22 2011 659 662
11. W. Hong, and J. Dowden Facile synthesis of N-6 adenosine modified analogue toward S-adenosyl methionine derived probe for protein arginine methyltransferases Chin. Chem. Lett. 22 2011 1439 1442
12. N.M. Yousif, K.Z. Gadalla, and S.M. Yassin Synthesis of O,O-dialkyl S-phenyl phosphorothiolates- and dithiolates Phosphorus Sulfur Silicon Relat. Elem. 60 1991 261 263
13. D.D. Liu, D.W. Chen, and Z.C. Chen Hypervalent iodine in synthesis. XII. A new and convenient method for preparation of O,O-dialkyl S-aryl phosphoro thiolates Synth. Commun. 22 1992 2903 2908
14. Y. Watanabe, S. Inoue, T. Yamamoto, and S. Ozaki Phosphorothioate synthesis based on the redox reaction of phosphite with tellurium(IV) chloride Synthesis 1995 1243 1244
15. S. Masson, J.F. Saint-Clair, and M. Saquet Two methods for the synthesis of (2-mercaptophenyl) phosphonic acid Synthesis 1993 485 486
16. R.G. Harvey, H.I. Jacobson, and E.V. Jensen Phosphonic acids. VI. The reaction of trivalent phosphorus esters with organic disulfides J. Am. Chem. Soc. 85 1963 1618 1623
17. Y.X. Gao, G. Tang, and Y.F. Zhao A novel and general method for the formation of S-aryl, Se-aryl, and Te-aryl phosphorochalcogenoates Synthesis 2009 1081
18. Y.H. Li, J.P. Li, and X. Xia A new synthesis of alkynyl tellurides promoted by CsOH and 4 Å MS Chin. Chem. Lett. 19 2008 1401 1402
19. K.P. Nandre, V.S. Patil, and S.V. Bhosale CsF mediated rapid condensation of 1,3-cyclohexadione with aromatic aldehydes: comparative study of conventional heating vs. ambient temperature Chin. Chem. Lett. 22 2011 777 780
20. A.H. Yu, R.H. Qiu, and N.Y. Tan Cesium hydroxide-catalyzed hydrothiolation of alkynyl selenides to highly stereo- and regioselectively synthesize (Z)-1-organoseleno-2-arylthio-1-alkenes Chin. Chem. Lett. 22 2011 687 690
21. B. Karimi, H. Hazarkhani, and D. Zareyee Trimethylchlorosilane (TMSCI) and cyanuric chloride (CC) catalyzed efficient oxidative coupling of thiols with dimethylsulfoxide Synthesis 2002 2513 2516
22. C.N. Yiannios, and J.V. Karabinos Oxidation of thiols by dimethyl sulfoxide J. Org. Chem. 28 1963 3246 3248
23. T.J. Wallace, A. Schriesheim, and W. Bartok The base-catalyzed oxidation of mercaptans. III. Role of the solvent and effect of mercaptan structure on the rate determining step J. Org. Chem. 28 1963 1311 1314