Three-Component Reaction between
Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot
Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

Nina K. Gusarova; Alexander V. Artem’ev; Ludmila A. Oparina; Nikita A. Kolyvanov; Svetlana F. Malysheva; Oksana V. Vysotskaya; Boris A. Trofimov

doi:10.1055/s-0031-1289655

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Synthesis 2012(3): 431-438
DOI: 10.1055/s-0031-1289655

PAPER

Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

Nina K. Gusarova, Alexander V. Artem’ev, Ludmila A. Oparina, Nikita A. Kolyvanov, Svetlana F. Malysheva, Oksana V. Vysotskaya, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;

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Publication History

Received 8 November 2011
Publication Date:
23 December 2011 (online)

Abstract
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Abstract

A family of previously unknown phosphinodiselenoic esters containing a selenoacetal moiety, R^² ₂P(=Se)SeCH(Me)OR^¹ (R^¹, R^² = alkyl, aryl, etc.), were synthesized by means of a three-component reaction between the elemental selenium and the corresponding vinyl ether and secondary phosphine. The reaction proceeds readily in 1,4-dioxane at 90 ˚C for 1-1.5 hours and gives the phosphinodiselenoic esters quantitatively and in an entirely atom-economic manner. The reaction proceeds through electrophilic addition to the electron-rich double bond of the phosphinodiselenoic acids generated in situ.

Key words

phosphines - multicomponent reactions - phosphorus - selenium - phosphinodiselenoate esters

References

1 Gusarova NK. Artem’ev AV. Malysheva SF. Tarasova OA. Trofimov BA. Tetrahedron Lett. 2011, 52: 6985

Google Scholar
For details of the biological significance and pharmacological activity of organoselenium compounds, see:
2a
National Research Council Subcommittee on Selenium Selenium in Nutrition, Revised Edition; National Academy Press: Washington (DC, USA), 1983.

Google Scholar
2b Mugesh G. du Mont W.-W. Sies H. Chem. Rev. 2001, 101: 2125

Google Scholar
2c Parker JN. Parker PM. Selenium: A Medical Dictionary, Bibliography, and Annotated Research Guide to Internet References Icon Health Publications; San Diego: 2004.

Google Scholar
2d Nogueira CW. Zeni G. Rocha JBT. Chem. Rev. 2004, 104: 6255

Google Scholar
2e Reilly C. Selenium in Food and Health Springer; New York: 2006.

Google Scholar
2f Selenium: Its Molecular Biology and Role in Human Health: Hatfield D. L., Berry M. J., Gladyshev V. N. 2nd ed.: Springer; New York: 2006.

Google Scholar
2g Divac VM. Bugarčić ZM. Synthesis 2009, 3684

Google Scholar
2h Ganesh V. Chandrasekaran S. Synthesis 2009, 3267

Google Scholar
2i Ren K. Wang M. Liu P. Wang L. Synthesis 2010, 1078

Google Scholar
2j Kálai T. Bagi N. Jekö J. Berente Z. Hideg K. Synthesis 2010, 1702

Google Scholar
2k Braga AL. Wessjohann LA. Taube PS. Galetto FZ. de Andrade FM. Synthesis 2010, 3131

Google Scholar
3a Mel’nikov NN. Novozhilov KV. Pylova TN. The Pesticide Chemistry Moscow, 1980;

Google Scholar
3b Matolcsy G. Nádasy M. Andriska V. Pesticide Chemistry Elsevier; Amsterdam: 1988.

Google Scholar
For recent examples of the use of P-Se compounds as capping agents and selenium sources for syntheses of selenium-containing nanomaterials, see:
4a Hsu Y.-J. Hung C.-M. Lin Y.-F. Liaw B.-J. Lobana TS. Lu S.-Y. Liu CW. Chem. Mater. 2006, 18: 3323

Google Scholar
4b Lin Y.-F. Chang H.-W. Lu S.-Y. Liu CW. J. Phys. Chem. C. 2007, 111: 18538

Google Scholar
4c Chang H.-W. Sarkar B. Liu CW. Cryst. Growth Des. 2007, 7: 2691

Google Scholar
4d Ahmad K. Afzaal M. O’Brien P. Hua G. Woollins JD. Chem. Mater. 2010, 22: 4619

Google Scholar
4e Malik MA. Afzaal M. O’Brien P. Chem. Rev. 2010, 110: 4417

Google Scholar
4f Owen JS. Chan EM. Liu H. Alivisatos AP. J. Am. Chem. Soc. 2010, 132: 18206

Google Scholar
4g Cossairt BM. Owen JS. Chem. Mater. 2011, 23: 3114

Google Scholar
For applications of phosphinodiselenoates in the preparation of nanomaterials, see:
5a Nguyen CQ. Afzaal M. Malik MA. Helliwell M. Raftery J. O’Brien P. J. Organomet. Chem. 2007, 692: 2669

Google Scholar
5b Kawai T, Hasegawa Y, and Adachi T. inventors; WO 2007102271. ; Chem. Abstr. 2007, 147, 368034

Google Scholar
5c Panneerselvam A. Nguyen CQ. Waters J. Malik MA. O’Brien P. Raftery J. Helliwell M. Dalton Trans. 2008, 4499

Google Scholar
5d Hasegawa Y. Adachi T. Tanaka A. Afzaal M. O’Brien P. Doi T. Hinatsu Y. Fujita K. Tanaka K. Kawai T. J. Am. Chem. Soc. 2008, 130: 5710

Google Scholar
5e Maneeprakorn W. Nguyen CQ. Malik MA. O’Brien P. Raftery J. Dalton Trans. 2009, 2103

Google Scholar
5f Panneerselvam A. Nguyen CQ. Malik MA. O’Brien P. Raftery J. J. Mater. Chem. 2009, 19: 419

Google Scholar
5g Tanaka A. Adachi T.-a. Hasegawa Y. Kawai T. J. Alloys Compd. 2009, 488: 538

Google Scholar
5h Maneeprakorn W. Malik MA. O’Brien P. J. Mater. Chem. 2010, 20: 2329

Google Scholar
6a Murai T. Kimura T. Curr. Org. Chem. 2006, 10: 1963

Google Scholar
6b Davies R. In Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium Devillanova FA. Royal Society of Chemistry; Cambridge: 2007. Chap. 5. p.286

Google Scholar
6c Sarkar B. Fang C.-S. You L.-Y. Wang J.-C. Liu CW. New J. Chem. 2009, 33: 626

Google Scholar
6d Selenium and Tellurium Chemistry: From Small Molecules to Biomolecules and Materials Woollins JD. Laitinen RS. Springer; Heidelberg: 2011.

Google Scholar
6e Artem’ev AV. Gusarova NK. Malysheva SF. Trofimov BA. Org. Prep. Proced. Int. 2011, 43: 381

Google Scholar
6f Artem’ev AV. Chernysheva NA. Gusarova NK. Malysheva SF. Yas’ko SV. Albanov AI. Trofimov BA. Synthesis 2011, 1309

Google Scholar
For applications of P-Se compounds as selenium-donating ligands, see:
7a Shi M. Wang C.-J. Zhang W. Chem. Eur. J. 2004, 10: 5507

Google Scholar
7b Gray IP. Slawin AMZ. Woollins JD. Dalton Trans. 2005, 2188

Google Scholar
7c Lobana TS. Wang J.-C. Liu CW. Coord. Chem. Rev. 2007, 251: 91

Google Scholar
7d Liu CW. Sarkar B. Huang Y.-J. Liao P.-K. Wang J.-C. Saillard J.-Y. Kahlal S. J. Am. Chem. Soc. 2009, 131: 11222

Google Scholar
7e Davies RP. Martinelli MG. Patel L. White AJP. Inorg. Chem. 2010, 49: 4626

Google Scholar
7f Liu CW. Chang H.-W. Sarkar B. Saillard J.-Y. Kahlal S. Wu Y.-Y. Inorg. Chem. 2010, 49: 468

Google Scholar
7g You H.-J. Fang C.-S. Lin J.-L. Sun S.-S. Liu CW. Inorg. Chem. 2010, 49: 7641

Google Scholar
7h Hua G. Randall RAM. Slawin AMZ. Woollins JD. Z. Anorg. Allg. Chem. 2011, 637: 1800

Google Scholar
8a Moon J. Nam H. Kim S. Ryu J. Han C. Lee C. Lee S. Tetrahedron Lett. 2008, 49: 5137

Google Scholar
8b Song E. Jo Y. Bae G. Oh I.-K. Jung HM. Lee S. Bull. Korean Chem. Soc. 2009, 30: 2129

Google Scholar
9a Krief A. Bousbaa J. Tetrahedron Lett. 1997, 38: 6291

Google Scholar
9b Sasaki M. Inoue M. Noguchi T. Takeichi A. Tachibana K. Tetrahedron Lett. 1998, 39: 2783

Google Scholar
9c Delouvrié B. Fensterbank L. Lacôte E. Malacria M. J. Am. Chem. Soc. 1999, 121: 11395

Google Scholar
9d Shimada K. Kikuta Y. Koganebuchi H. Yonezawa F. Aoyagi S. Takikawa Y. Tetrahedron Lett. 2000, 41: 4637

Google Scholar
9e Sasaki M. Noguchi T. Tachibana K. J. Org. Chem. 2002, 67: 3301

Google Scholar
9f Deleuze A. Sollogoub M. Blériot Y. Marrot J. Sinaÿ P. Eur. J. Org. Chem. 2003, 2678

Google Scholar
9g Tsuchii K. Doi M. Hirao T. Ogawa A. Angew. Chem. Int. Ed. 2003, 42: 3490

Google Scholar
9h Davidson JEP. Gilmour R. Ducki S. Davies JE. Green R. Burton JW. Holmes AB. Synlett 2004, 1434

Google Scholar
9i Tsuchii K. Doi M. Ogawa I. Einaga Y. Ogawa A. Bull. Chem. Soc. Jpn. 2005, 78: 1534

Google Scholar
9j Yamamoto T. Moriura E. Sawa A. Yoshimatsu M. Chem. Lett. 2008, 37: 1046

Google Scholar
9k Frankie Mak SY. Chiang GCH. Davidson JEP. Davies JE. Burton JW. Holmes AB. Ayscough A. Pain G. Tetrahedron: Asymmetry 2009, 20: 921

Google Scholar
For details on the accessibility of vinyl ethers, see:
10a Trofimov BA. Curr. Org. Chem. 2002, 6: 1121

Google Scholar
10b Trofimov BA. Gusarova NK. Russ. Chem. Rev. 2007, 76: 507

Google Scholar
10c Winternheimer DJ. Shade RE. Merlic CA. Synthesis 2010, 2497

Google Scholar
11 Trofimov BA. Parshina LN. Oparina LA. Tantsyrev AP. Khil’ko MYu. Vysotskaya OV. Stepanov AV. Gusarova NK. Henkelmann J. Tetrahedron 2007, 63: 11661

Google Scholar
12a Sukhov BG. Gusarova NK. Ivanova NI. Bogdanova MV. Kazheva ON. Alexandrov GG. D’yachenko OA. Sinegovskaya LM. Malysheva SF. Trofimov BA. J. Struct. Chem. 2005, 46: 1066

Google Scholar
12b Dornhaus F. Lerner H.-W. Michael B. Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, 63: o4917

Google Scholar
13a Kuchen W. Knop B. Angew. Chem., Int. Ed. Engl. 1965, 4: 244

Google Scholar
13b Kuchen W. Knop B. Chem. Ber. 1966, 99: 1663

Google Scholar
14 Artem’ev AV. Gusarova NK. Malysheva SF. Ushakov IA. Trofimov BA. Tetrahedron Lett. 2010, 51: 2141

Google Scholar
15 Oparina LA. Shaikhudinova SI. Parshina LN. Vysotskaya OV. Preiss Th. Henkelmann J. Trofimov BA. Russ. J. Org. Chem. 2005, 41: 656

Google Scholar
16 Trofimov BA. Khil’ko MYa. Nedolya NA. Demanov YuK. Vyalykh EP. Zh. Org. Khim. 1982, 18: 744 ; Chem. Abstr. 1982, 97, 55265

Google Scholar
17 Oparina LA. Vysotskaya OV. Stepanov AV. Gusarova NK. Trofimov BA. Russ. J. Org. Chem. 2009, 45: 134

Google Scholar
18 Lavrov VI. Oparina LA. Parshina LN. Vins VV. Trofimov BA. Russ. J. Appl. Chem. 1990, 63: 835

Google Scholar
19 Trofimov BA. Brandsma L. Arbuzova SN. Malysheva SF. Gusarova NK. Tetrahedron Lett. 1994, 35: 7647

Google Scholar