Catalyst-Free and Solvent-Free Addition of P(Se)–H Species to Alkenes: A Straightforward Access to Tertiary Phosphine Selenides

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.

Key words

addition - alkenes - green method - phosphine selenides - regioselectivity

• References


For review, see:
• 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

For example, see:
• 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

From recent examples, see:
• 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