A Novel and General Method for
the Formation of S-Aryl, Se-Aryl, and Te-Aryl
Phosphorochalcogenoates

Yu-Xing Gao; Guo Tang; Yu Cao; Yu-Fen Zhao

doi:10.1055/s-0028-1088012

PAPER

A Novel and General Method for the Formation of S-Aryl, Se-Aryl, and Te-Aryl Phosphorochalcogenoates

Yu-Xing Gao^a, Guo Tang*^a, Yu Cao^a, Yu-Fen Zhao*^a,b
^a Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China
^b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(592)2185780; e-Mail: t12g21@xmu.edu.cn; e-Mail: yfzhao@xmu.edu.cn;

Abstract

All articles of this category

Abstract

A new and general method for the synthesis of S-, Se-, and Te-aryl phosphorochalcogenoates (chalcogenophosphates) has been developed. S-P, Se-P, and Te-P bonds were formed by the coupling of readily available dialkyl phosphites with diaryl dichalcogenides at 30 ˚C in dimethyl sulfoxide in the presence of catalytic amounts of copper iodide and diethylamine. The reaction proceeded smoothly without exclusion of moisture or air.

Key words

Lewis acids - selenium - phosphorylation - sulfur - tellurium

Full Text

References

1a Han L.-B. Choi N. Tanaka M. J. Am. Chem. Soc. 1996, 118: 7000

1b Lopin C. Gouhier G. Gautier A. Piettre SR. J. Org. Chem. 2003, 68: 9916

1c Yousif NM. Gadalla KZ. Yassin SM. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 60: 261

1d Fukuoka M. Shuto S. Minakawa N. Ueno Y. Matsuda A. J. Org. Chem. 2000, 65: 5238

1e Fukuoka M. Shuto S. Minakawa N. Ueno Y. Matsuda A. Tetrahedron Lett. 1999, 40: 5361

1f Huang L.-J. Zhao Y.-Y. Yuan L. Min J.-M. Zhang L.-H. J. Med. Chem. 2002, 45: 5340

1g Marinozzi M. Fulco MC. Rizzo R. Pellicciari R. Synlett 2004, 1027

1h Glass RS. Singh WP. Jung W. Veres Z. Scholz TD. Stadtman T. Biochemistry 1993, 53: 15085

2a Jacob L. Julia M. Pfeiffer B. Rolando C. Tetrahedron Lett. 1983, 24: 4327

2b Sekine M. Hata T. J. Am. Chem. Soc. 1983, 105: 2044

2c Seio K. Wada T. Sakamoto K. Yokoyama S. Sekine M. Tetrahedron Lett. 1995, 36: 9515

2d Seio K. Wada T. Sakamoto K. Yokoyama S. Sekine M. J. Org. Chem. 1998, 63: 1429

3 Han L.-B. Tanaka M. Chem. Lett. 1999, 863

4a Masson S. Saint-Clair J.-F. Saquet M. Synthesis 1993, 485

4b Hayashi M. Miura T. Matsuchika K. Watanabe Y. Synthesis 2004, 1481

5a Herpin TF. Houlton JS. Motherwell WB. Roberts BP. Weibel J.-M. Chem. Commun. 1996, 613

5b Herpin TF. Motherwell WB. Roberts BP. Roland S. Weibel J.-M. Tetrahedron 1997, 53: 15085

6 Chen DJ. Chen ZC. J. Chem. Res., Synop. 2000, 370

7a Harvey RG. Jacobson HI. Jensen EV. J. Am. Chem. Soc. 1963, 85: 1618

7b Garegg PJ. Regberg T. Stawinski J. Strömberg R. J. Chem. Soc., Perkin Trans. 1 1987, 1269

7c Müller CE. Roth HJ. Tetrahedron Lett. 1990, 31: 501

7d Watanabe Y. Inoue S. Yamamoto T. Ozaki S. Synthesis 1995, 1243

7e Brill WK.-D. Tetrahedron Lett. 1995, 36: 703

7f Kataevand EG. Mannafov TG. Zh. Obshch. Khim. 1966, 36: 254

7g Chen D.-J. Chen Z.-C. Synth. Commun. 2001, 31: 421

7h Liu D.-D. Chen D.-W. Chen Z.-C. Synth. Commun. 1992, 22: 2903

8 Xu Q. Liang C.-G. Huang X. Synth. Commun. 2003, 33: 2777

9a Chen J.-M. Huang X. Synth. Commun. 2004, 34: 1745

9b Chen J.-M. Lin X.-J. Huang X. J. Chem. Res., Synop. 2004, 43

10 Petragnani N. Tellurium in Organic Synthesis Academic Press; London: 1994.

11 Bieber LW. Silva MF. Menezes PH. Tetrahedron Lett. 2004, 45: 2735

12 Karimi B. Hazarkhani H. Zareyee D. Synthesis 2002, 2513

13a Clive DLJ. Menchen SM. J. Chem. Soc., Chem. Commun. 1977, 658

13b Clive DLJ. Menchen SM. J. Org. Chem. 1980, 45: 2347