Synthesis 2015; 47(11): 1611-1622
DOI: 10.1055/s-0034-1380408
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst- and Solvent-Free Rapid Addition of Secondary Phosphine Chalcogenides to Aldehydes: Another Click Chemistry

Nina K. Gusarova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Nina I. Ivanova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Pavel A. Volkov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Kseniya O. Khrapova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Luydmila I. Larina
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Vladimir I. Smirnov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Tatyana N. Borodina
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author Affiliations
Further Information

Publication History

Received: 24 December 2014

Accepted after revision: 30 January 2015

Publication Date:
09 March 2015 (online)


Abstract

An efficient catalyst- and solvent-free method for the synthesis of tertiary α-hydroxyphosphine chalcogenides, via the almost quantitative addition of secondary phosphine chalcogenides to diverse aldehydes under mild conditions (20–52 °C, from 10 min to 5 h), is reported.

Supporting Information

 
  • References

    • 1a Gusarova NK, Reutskaya AM, Ivanova NI, Medvedeva AS, Demina MM, Novopashin PS, Afonin AV, Albanov AI, Trofimov BA. J. Organomet. Chem. 2002; 659: 172
    • 1b Gusarova NK, Arbuzova SN, Reutskaya AM, Ivanova NI, Baikalova LV, Sinegovskaya LM, Chipanina NN, Afonin AV, Zyryanova IA. Chem. Heterocycl. Compd. 2002; 38: 65
    • 1c Ivanova NI, Reutskaya AM, Gusarova NK, Medvedeva SA, Afonin AV, Ushakov IA, Tatarinova AA, Trofimov BA. Russ. J. Gen. Chem. 2003; 73: 1354
    • 1d Ivanova NI, Gusarova NK, Nikitina EA, Albanov AI, Sinegovskaya LM, Nikitin MV, Konovalova NA, Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 7
    • 1e Ivanova NI, Gusarova NK, Nikitina EA, Medvedeva SA, Al’pert ML, Trofimov BA. Chem. Heterocycl. Compd. 2004; 40: 426
    • 1f Priya S, Balakrishna MS, Mobin SM. Polyhedron 2005; 24: 1641
    • 1g Liu W.-Y, Huo P, Gao Y.-X, Liu P, Zhao Y.-F. Acta Crystallogr., Sect. E 2007; 63: 1008
    • 1h Liu W.-Y, Huo P. Acta Crystallogr., Sect. E 2008; 64: 233
    • 1i Yuan X.-L, Liu W.-Y, Huo P, Mei G.-O. Acta Crystallogr., Sect. E 2010; 66: 2331
    • 1j Keglevich G, To’th VR, Drahos L. Heteroat. Chem. 2011; 22: 15
    • 1k Ivanova NI, Volkov PA, Gusarova NK, Larina LI, Trofimov BA. Russ. J. Gen. Chem. 2011; 81: 315
    • 1l Luo X, Zhou Z, Li X, Liang X, Ye J. RSC Adv. 2011; 1: 698
    • 1m Zheng J, Feng X, Yu Y, Zhen X, Zhao Y. Phosphorus, Sulfur Silicon Relat. Elem. 2013; 188: 1080
    • 1n Kortmann FA, Chang M.-C, Otten E, Couzijn EP. A, Lutz M, Minnaard AJ. Chem. Sci. 2014; 5: 1322
    • 2a Trofimov BA, Gusarova NK, Ivanova NI, Konovalova NA, Bogdanova MV, Albanov AI, Avseenko ND, Sukhov BG. Russ. J. Gen. Chem. 2004; 74: 1625
    • 2b Ivanova NI, Baikalova LV, Konovalova NA, Zyryanova IA, Albanov AI, Sinegovskaya LM, Kukhareva VA, Tatarinova AA, Avseenko ND, Sukhov BG, Gusarova NK, Trofimov BA. Chem. Heterocycl. Compd. 2005; 41: 317
    • 2c Ivanova NI, Volkov PA, Baikalova LV, Gusarova NK, Trofimov BA. Chem. Heterocycl. Compd. 2008; 44: 1359
  • 3 Gusarova NK, Ivanova NI, Konovalova NA, Sukhov BG, Baikalova LV, Sinegovskaya LM, Pavlov DV, Trofimov BA. Synthesis 2006; 4159
  • 4 Clark HJ, Wang R, Alper H. J. Org. Chem. 2002; 67: 6224
  • 5 Chen MJ, Chen CR, Tan Y, Huang JQ, Wang XL, Chen L, Wang YZ. Ind. Eng. Chem. Res. 2014;  53:  1160
  • 6 Moiseev DV, James BR, Hu TQ. Phosphorus, Sulfur Silicon Relat. Elem. 2012; 187: 433
    • 7a Cristau HJ, Brahic C, Pirat JL. Tetrahedron 2001;  57:  9149
    • 7b Nawrot B, Michalak O, Clercq ED, Stec WJ. Antivir. Chem. Chemother. 2004; 15: 319
    • 8a Trofimov BA, Gusarova NK. Mendeleev Commun. 2009; 19: 295
    • 8b Gusarova NK, Arbuzova SN, Trofimov BA. Pure Appl. Chem. 2012; 84: 439
  • 9 Well M, Schmutzler R. Phosphorus, Sulfur Silicon Relat. Elem. 1992; 72: 171
    • 10a Afonin AV, Baikalova LV, Domnina ES. Russ. Chem. Bull. 1996; 45: 1137
    • 10b Baikalova LV, Domnina ES, Chipanina NN, Afonin AV, Shulunova AM. Russ. Chem. Bull. 1999; 48: 962
    • 11a Peters G. J. Am. Chem. Soc. 1960; 82: 4751
    • 11b Maier L. Helv. Chim. Acta 1966; 49: 1000
  • 12 Bodenhausen G, Ruben D. J. Chem. Phys. Lett. 1980; 69: 185
  • 13 Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093
  • 14 CCDC 1038369–1038371 contain the supplementary crystallographic data of compounds 12l, 18d, and 18m, respectively. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.
  • 15 Sheldrick GM. Acta Crystallogr., Sect. D 2008; 64: 112
  • 16 Emoto T, Gomi H, Yoshifuji M, Okazaki R, Inamoto N. Bull. Chem. Soc. Jpn. 1974; 47: 2449