One-Pot Reaction of Secondary Phosphine Selenides with Selenium and Nitrogen Bases: A Novel Synthesis of Diorganodiselenophosphinates

Abstract

A three-component reaction of secondary phosphine selenides­ R₂P(Se)H [R = PhCH₂CH₂, PhCH(Me)CH₂, 4-t-BuC₆H₄CH₂CH₂, (2-methyl-5-pyridyl)CH₂CH₂, Ph], elemental selenium, and primary, secondary, and tertiary amines and diamines proceeds under mild conditions (25-85 ˚C, 1-90 min) in tetrahydrofuran-ethanol as medium to give previously unknown mono-, di-, and triorganoammonium salts of diorganodiselenophosphinates in high yields (up to 99%).

Key words

secondary phosphine selenides - elemental selenium - amines - three-component atom-economic reactions - diselenophosphinates - phosphorus compounds

References

• 1a Davies RP. Martinelli MG. Inorg. Chem.  2002,  41:  348 
• 1b Davies RP. Martinelli MG. Wheatley AEH. White AJP. Williams DJ. Eur. J. Inorg. Chem.  2003,  3409 
• 1c Davies RP. Francis CV. Jurd APS. Martinelli MG. White AJP. Williams DJ. Inorg. Chem.  2004,  43:  4802 
• 2 Nguyen CQ. Afzaal M. Malik MA. Helliwell M. Raftery J. O’Brien P. J. Organomet. Chem.  2007,  692:  2669 
• 3a Bwembya GC. Song X. Bochmann M. Chem. Vap. Deposition  1995,  1:  78 
• 3b Gubin SP. Kataeva NA. Khomutov GB. Russ. Chem. Bull.  2005,  54:  827 
• 3c Nguyen CQ. Adeogun A. Afzaal M. Malik MA. O’Brien P. Chem. Commun.  2006,  2182 
• 3d Fan D. Afzaal M. Mallik MA. Nguyen CQ. O’Brien P. Thomas PJ. Coord. Chem. Rev.  2007,  251:  1878 
• 3e 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 
• For reviews, see:
• 4a Lobana TS. Wang J.-C. Liu CW. Coord. Chem. Rev.  2007,  251:  91 
• 4b Kuchen W. Knop B. Angew. Chem., Int. Ed. Engl.  1965,  4:  244 
• 4c Kuchen W. Knop B. Chem. Ber.  1966,  99:  1663 
• 4d Hertel H. Kuchen W. Chem. Ber.  1971,  104:  1740 
• 4e Esperas S. Husebye S. Acta Chem. Scand.  1973,  27:  1827 
• 4f Muller A. Rao VVK. Christophliemk P. J. Inorg. Nucl. Chem.  1974,  36:  472 
• 4g Lucio Gelmini L. Stephan DW. Organometallics  1987,  6:  1515 
• 5a Rickelton WA. Boyl R. J. Sep. Sci. Tech.  1988,  23:  1227 
• 5b Flett DS. J. Organomet. Chem.  2005,  690:  2426 
• 6a Mashkovskii MD. Drugs (in Russian)   Vol. 2, 12th ed.:  Medicina; Moscow: 1989.  p.360 
• 6b Abdulina GA. Gazaliev AM. Baikenova GG. Fazylov SD. Kudaibergenova S. Khim.-Farm. Zh. (in Russian)  2002,  3:  11. 
• 7 Kimura T. Murai T. J. Org. Chem.  2005,  70:  952 
• 8 Moon J. Nam H. Kim S. Ryu J. Han C. Lee C. Lee S. Tetrahedron Lett.  2008,  49:  5137 
• 9 Mashkovskii MD. Drugs (in Russian)   Vols. 1,2, 12th ed.:  Medicina; Moscow: 1989. 
• For reviews, see:
• 10a Greaves TL. Drummond CJ. Chem. Rev.  2008,  108:  206 
• 10b Wasserscheid P. Welton T. Ionic Liquids in Synthesis   Wiley; Weinheim: 2008. 
• 11a Trofimov BA. Brandsma L. Arbuzova SN. Malysheva SF. Gusarova NK. Tetrahedron Lett.  1994,  35:  7647 
• 11b Sukhov BG. Gusarova NK. Ivanova NI. Bogdanova MV. Kazheva ON. Alexandrov GG. Dyachenko OA. Sinegovskaya LM. Malysheva SF. Trofimov BA. J. Struct. Chem.  2005,  46:  1066 
• 11c Gusarova NK. Malysheva SF. Kuimov VA. Belogorlova NA. Mikhailenko VL. Trofimov BA. Mendeleev Commun.  2008,  18:  260 
• 11d Gusarova NK. Ivanova NI. Volkov PA. Larina LI. Synthesis  2008,  3523 
• 12a Burakova EA. Kovalev NA. Kuznetsova IL. Zenkova MA. Vlasov VV. Sil’nikov VN. Russ. J. Bioorg. Chem.  2007,  35:  563 
• 12b Kuznetsova IL. Zenkova MA. Vlasov VV. Russ. Chem. Rev.  2007,  76:  305 
• 13 Perrin DD. Armarego WLF. Perrin DR. Purification of Laboratory Chemicals   2nd ed.:  Pergamon; Oxford: 1980. 
• 14 Sheldrick GM. SHELXS 97   University of Göttingen; Germany: 1997.