A Simple Copper Salt-Catalyzed Synthesis of Unsymmetrical Diaryl Selenides and Tellurides from Arylboronic Acids with Diphenyl Diselenide and Ditelluride

Lei Wang; Min Wang; Fuping Huang

doi:10.1055/s-2005-871936

LETTER

A Simple Copper Salt-Catalyzed Synthesis of Unsymmetrical Diaryl Selenides and Tellurides from Arylboronic Acids with Diphenyl Diselenide and Ditelluride

Lei Wang*^a,b, Min Wang^a, Fuping Huang^a
^a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;

Abstract

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Abstract

In the presence of a catalytic amount of simple copper salt, the reaction of arylboronic acids with diphenyl diselenide and ditelluride was accomplished without any additive to afford the corresponding unsymmetrical diarylselenides and tellurides in good yields.

Key words

copper salt - diaryl selenides - diaryl tellurides - arylboronic acids - diphenyl diselenide - diphenyl ditelluride

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Referenzen

References

1a The Chemistry of Organic Selenium and Tellurium Compounds Vol. 1: Patai S. Rappoport Z. Wiley; Chichester: 1986.

1b The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2: Patai S. Rappoport Z. Wiley; Chichester: 1987.

1c Krief A. In Comprehensive Organometallic Chemistry Trost BM. Pergamon Press; Oxford: 1991. p.85-192

1d Krief A. In Comprehensive Organometallic Chemistry II Vol. 11: Abel EW. Stone FGA. Wilkinson G. Pergamon Press; New York: 1995. Chap. 13.

1e Organoselenium Chemistry: A Practical Approach Back TG. Oxford University Press; New York: 1999.

1f Ip C. J. Nutr. 1998, 128: 1845

1g Ip C. Lisk DJ. Ganther H. Thompson HJ. Anticancer Res. 1997, 17: 3195

1h Organoselenium Chemistry, In Topics in Current Chemistry Vol. 208: Wirth T. Springer-Verlag; Heidelberg: 2000.

2a Ranu BC. Mandal T. J. Org. Chem. 2004, 69: 5793

2b Ranu BC. Mandal T. Samanta S. Org. Lett. 2003, 5: 1439

2c Bao W. Zheng Y. Zhang Y. Zhou J. Tetrahedron Lett. 1996, 37: 9333

2d Bao W. Zhang Y. Synlett 1996, 1187

2e Fukuzawa S. Niimoto Y. Fujinami T. Sakai S. Heteroat. Chem. 1990, 1: 491

2f Sakakibara M. Katsumata K. Watanabe Y. Toru T. Ueno Y. Synthesis 1992, 377

2g Detty MR. J. Org. Chem. 1980, 45: 274

2h Wang L. Zhang Y. Heteroat. Chem. 1999, 10: 203

2i Nishino T. Okada M. Kuroki T. Watanabe T. Nishiyama Y. Sonoda N. J. Org. Chem. 2002, 67: 8696

2j Bieber LW. Sa ACPF. Menezes PH. Goncalves SMC. Tetrahedron Lett. 2001, 42: 4597

3a Cristau HJ. Chabaud B. Labaudiniere R. Christol H. Organometallics 1985, 4: 657

3b Zhang Y. Guo H. Heteroat. Chem. 2001, 12: 539

3c Vasil’ev AA. Engman L. Storm JP. Andersson C.-M. Organometallics 1999, 18: 1318

3d Gujadhur RK. Venkataraman D. Tetrahedron Lett. 2003, 44: 81

3e Osuka A. Ohmasa N. Suzuki H. Synthesis 1982, 857

3f In the absence of any additive, the reaction of with iodobenzene in liquid ammonia only get 3% yield of diphenylselenide. See: Penenory AB. Pierini AB. Rossi RA. J. Org. Chem. 1984, 49: 3834

4a Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

4b Suzuki A. J. Organomet. Chem. 1999, 576: 147

5a Lam PYS. Vincent G. Bonne D. Clark CG. Tetrahedron Lett. 2003, 44: 4927

5b Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

6 Chan DMT. Monaco KL. Wang RP. Winters MP. Tetrahedron Lett. 1998, 39: 2933

7a Tsukamoto H. Sato M. Kondo Y. Chem. Commun. 2004, 1200

7b Kabalka GW. Dong G. Venkataiah B. Org. Lett. 2003, 5: 893

8a Lan JB. Chen L. Yu XQ. You JS. Xie RG. Chem. Commun. 2004, 188

8b Collman JP. Zhong M. Zhang C. Costanzo S. J. Org. Chem. 2001, 66: 7892

8c Lam PYS. Clark CG. Saubern S. Adams J. Winters MP. Chan DMT. Combs A. Tetrahedron Lett. 1998, 39: 2941

9 Zou G. Zhu J. Tang J. Tetrahedron Lett. 2003, 44: 8709

10 Patel SJ. Jamison TF. Angew. Chem. Int. Ed. 2003, 42: 1364

11 Yoshida M. Gotou T. Ihara M. Chem. Commun. 2004, 1124

12a Tang ZY. Hu QS. J. Am. Chem. Soc. 2004, 126: 3058

12b Bandgar BP. Bettigeri SV. Phopase J. Org. Lett. 2004, 6: 2105

13a Principles and Applications of Organotransition Metal Chemistry Collman JP. Hegedus LS. Norton JR. Finke RG. University Science; Mill Valley CA: 1987.

13b Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998.

14a Taniguchi N. Onami T. Synlett 2003, 829

14b Taniguchi N. Onami T. J. Org. Chem. 2004, 69: 915

15a Welton T. Chem. Rev. 1999, 99: 2071

15b Wasserschield P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772

15c DuPont J. De Souza RF. Suarez PAZ. Chem. Rev. 2002, 102: 3667

16 Kabalka GW. Venkataiah B. Tetrahedron Lett. 2002, 43: 3703

17a Molander GA. Ribagorda M. J. Am. Chem. Soc. 2003, 125: 11148

17b Vedejs E. Chapman RW. Fields SC. Lin S. Schrimpf MR. J. Org. Chem. 1995, 60: 3020

17c Darses S. Michaud G. Genêt JP. Tetrahedron Lett. 1998, 39: 5045

17d Molander GA. Rivero MR. Org. Lett. 2002, 4: 107

17e Molander GA. Biolatto B. J. Org. Chem. 2003, 68: 4302

17f Batey RA. Thadani AN. Org. Lett. 1999, 1: 1683

17g Thadani AN. Batey RA. Org. Lett. 2002, 4: 3827

17h Kabalka GW. Dong G. Venkataiah B. Tetrahedron Lett. 2004, 45: 5139

17i Kabalka GW. Venkataiah B. Dong G. Org. Lett. 2003, 5: 3803

17j Barder TE. Buchwald SL. Org. Lett. 2004, 6: 2649