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Synthesis 2009(19): 3332-3338
DOI: 10.1055/s-0029-1216948
DOI: 10.1055/s-0029-1216948
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Reaction of Secondary Phosphine Selenides with Selenium and Nitrogen Bases: A Novel Synthesis of Diorganodiselenophosphinates
Further Information
Received
15 May 2009
Publication Date:
21 August 2009 (online)
Publication History
Publication Date:
21 August 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200919/lookinside/thumbnails/10.1055-s-0029-1216948-1.jpg)
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
-
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.