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Synthesis 2014; 46(19): 2656-2662
DOI: 10.1055/s-0034-1378357
DOI: 10.1055/s-0034-1378357
paper
Catalyst-Free and Solvent-Free Addition of P(Se)–H Species to Alkenes: A Straightforward Access to Tertiary Phosphine Selenides
Further Information
Publication History
Received: 06 April 2014
Accepted after revision: 30 May 2014
Publication Date:
14 July 2014 (online)
Abstract
Under catalyst- and solvent-free conditions, secondary phosphine selenides easily add to diverse alkenes [acrylonitrile, allyl alcohol, styrene, vinyl ethers, vinyl sulfides, and trimethyl(vinyl)silane] at 80 °C (3–20 h) to give anti-Markovnikov adducts in 70–95% yield.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Delacroix O, Gaumont AC. Curr. Org. Chem. 2005; 9: 1851
- 1b Arbuzova SN, Gusarova NK, Trofimov BA. ARKIVOC 2006; (v): 12
- 1c Honaker MT, Hovland JM, Salvatore RN. Curr. Org. Synth. 2007; 4: 31
- 1d Xu Q, Han L.-B. J. Organomet. Chem. 2011; 696: 130
- 1e Gusarova NK, Arbuzova SN, Trofimov BA. Pure Appl. Chem. 2012; 84: 439
- 1f Xu Q, Zhou Y.-B, Zhao C.-Q, Yin S.-F, Han L.-B. Mini-Rev. Med. Chem. 2013; 13: 824
- 1g Pullarkat SA, Leung P.-H. Top. Organomet. Chem. 2013; 43: 145
- 1h Tanaka M. Top. Organomet. Chem. 2013; 43: 167
- 1i Koshti V, Gaikwad S, Chikkali SH. Coord. Chem. Rev. 2014; 265: 52
- 2a Bunlaksananusorn T, Knochel P. Tetrahedron Lett. 2002; 43: 5817
- 2b Fu X, Jiang Z, Tan C.-H. Chem. Commun. 2007; 5058
- 2c Perrier A, Comte V, Moïse C, Richard P, Le Gendre P. Eur. J. Org. Chem. 2010; 1562
- 3a Dombek BD. J. Org. Chem. 1978; 43: 3408
- 3b Malysheva SF, Gusarova NK, Belogorlova NA, Nikitin MV, Gendin DV, Trofimov BA. Russ. J. Gen. Chem. 1997; 67: 58
- 3c Routaboul L, Toulgoat F, Gatignol J, Lohier J.-F, Norah B, Delacroix O, Alayrac C, Taillefer M, Gaumont A.-C. Chem. Eur. J. 2013; 19: 8760
- 4a Leca D, Fensterbank L, Lacôte E, Malacria M. Chem. Soc. Rev. 2005; 34: 858
- 4b Oparina LA, Gusarova NK, Vysotskaya OV, Artem’ev AV, Kolyvanov NA, Trofimov BA. Synthesis 2014; 46: 653
- 5a Lobana TS, Mahajan P, Pannu AS, Hundal G, Butcher RJ. J. Coord. Chem. 2007; 60: 733
- 5b Kilpin KJ, Henderson W, Nicholson BK. Dalton Trans. 2010; 39: 1855
- 5c Pop A, Silvestru A, Gimeno MC, Laguna A, Kulcsar M, Arca M, Lippolis V, Pintus A. Dalton Trans. 2011; 40: 12479
- 5d Canales S, Villacampa MD, Laguna A, Gimeno MC. J. Organomet. Chem. 2014; 760: 84
- 6a Koh W, Yoon Y, Murray CB. Chem. Mater. 2011; 23: 1825
- 6b Vaughn DD, In S.-l, Schaak RE. ACS Nano 2011; 5: 8852
- 6c Boercker JE, Foos EE, Placencia D, Tischler JG. J. Am. Chem. Soc. 2013; 135: 15071
- 6d García-Rodríguez R, Liu H. J. Am. Chem. Soc. 2014; 136: 1968
- 7 Gusarova NK, Malysheva SF, Belogorlova NA, Sukhov BG, Trofimov BA. Synthesis 2007; 2849
- 8 Gusarova NK, Chernysheva NA, Yas’ko SV, Kazantseva TI, Ushakov IA, Trofimov BA. Synthesis 2008; 2743
- 9 Gusarova NK, Volkov PA, Ivanova NI, Chernysheva NA, Yas’ko SV, Albanov AI, Trofimov BA. Russ. J. Gen. Chem. 2010; 80: 1602
- 10 Gusarova NK, Chernysheva NA, Yas’ko SV, Klyba LV, Trofimov BA. Russ. J. Gen. Chem. 2011; 81: 2506
- 11 Gusarova NK, Malysheva SF, Belogorlova NA, Parshina LN, Trofimov BA. Synthesis 2011; 1777
- 12 Malysheva SF, Gusarova NK, Belogorlova NA, Kashik TV, Krivdin LB, Fedorov SV, Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 1838
- 13a Sheldon RA, Arends I, Hanefeld U. Green Chemistry and Catalysis . Wiley–VCH; Weinheim: 2007
- 13b Tundo P, Perosa A, Zecchini F. Methods and Reagents for Green Chemistry: An Introduction . Wiley; Hoboken: 2007
- 14a Stockland RA. Jr, Taylor RI, Thompson LE, Patel PB. Org. Lett. 2005; 7: 851
- 14b Lenker HK, Richard ME, Reese KP, Carter AF, Zawisky JD, Winter EF, Bergeron TW, Guydon KS, Stockland RA. Jr. J. Org. Chem. 2012; 77: 1378
- 15 Alonso F, Moglie Y, Radivoy G, Yus M. Green Chem. 2012; 14: 2699
- 16 Malysheva SF, Gusarova NK, Artem’ev AV, Belogorlova NA, Albanov AI, Borodina TN, Smirnov VI, Trofimov BA. Eur. J. Org. Chem. 2014; 2516
- 17a Trofimov BA, Brandsma L, Arbuzova SN, Malysheva SF, Gusarova NK. Tetrahedron Lett. 1994; 35: 7647
- 17b Gusarova NK, Malysheva SF, Kuimov VA, Belogorlova NA, Mikhailenko VL, Trofimov BA. Mendeleev Commun. 2008; 18: 260
- 18 Gusarova NK, Chernysheva NA, Yas’ko SV, Trofimov BA. Russ. Chem. Bull. 2013; 62: 438
- 19 Sheldrick GM. Acta Crystallogr., Sect. D 2008; 64: 112
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