Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(02): 263-271
DOI: 10.1055/s-0034-1379207
DOI: 10.1055/s-0034-1379207
paper
Catalyst- and Solvent-Free Stereoselective Addition of Secondary Phosphine Chalcogenides to Alkynes
Further Information
Publication History
Received: 23 July 2014
Accepted after revision: 03 September 2014
Publication Date:
23 October 2014 (online)
Abstract
The addition of secondary phosphine sulfides and selenides to alkynes proceeds readily (80 °C, 5–13 h) without catalysts or solvents to afford regio- and stereoselectively anti-Markovnikov adducts as tertiary alkenylphosphine chalcogenides of Z-configuration, in 60–94% yield.
Key words
addition reactions - alkynes - green chemistry - phosphine chalcogenides - regioselectivitySupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are copies of NMR spectra and details of the DFT computations.
- Supporting Information
-
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 Wauters I, Debrouwer W, Stevens CV. Beilstein J. Org. Chem. 2014; 10: 1064
- 2a Bartels B, Martin CG, Nelson A, Russell MG, Warren S. Tetrahedron Lett. 1998; 39: 1637
- 2b Ono Y, Han L.-B. Tetrahedron Lett. 2006; 47: 421
- 2c Science of Synthesis, Houben Weyl Methods of Molecular Transformations . Vol. 33. Georg Thieme Verlag KG; Stuttgart: 2007: 665–694, 701–710
- 2d Gonzalez-Nogal AM, Cuadrado P, Sarmentero MA. Tetrahedron 2010; 66: 9610
- 3a Julienne D, Toulgoat F, Delacroix O, Gaumont A.-C. Curr. Org. Chem. 2010; 14: 1195
- 3b Xi C, Yu B, Yan X, Tang N. Polyhedron 2013; 52: 1323
- 4a Glotova TE, Dvorko MYu, Arbuzova SN, Ushakov IA, Verkhoturova SI, Gusarova NK, Trofimov BA. Lett. Org. Chem. 2007; 4: 109
- 4b Greenberg S, Gibson GL, Stephan DW. Chem. Commun. 2009; 304
- 4c Dvorko MYu, Glotova TE, Ushakov IA, Gusarova NK. Russ. J. Org. Chem. 2010; 46: 485
- 5a Glueck DS. Top. Organomet. Chem. 2010; 31: 65
- 5b Xu Q, Han L.-B. J. Organomet. Chem. 2011; 696: 130
- 5c Xu Q, Zhou Y.-B, Zhao C.-Q, Yin S.-F, Han L.-B. Mini-Rev. Med. Chem. 2013; 13: 824
- 5d Pullarkat SA, Leung P.-H. Top. Organomet. Chem. 2013; 43: 145
- 5e Tanaka M. Top. Organomet. Chem. 2013; 43: 167
- 5f Koshti V, Gaikwad S, Chikkali SH. Coord. Chem. Rev. 2014; 265: 52
- 6a Semenzin D, Etemad-Moghadam G, Albouy D, Diallo O, Koenig M. J. Org. Chem. 1997; 62: 2414
- 6b Parsons AF, Sharpe DJ, Taylor P. Synlett 2005; 1
- 6c Jessop CM, Parsons AF, Routledge A, Irvine DJ. Eur. J. Org. Chem. 2006; 1547
- 7a Mimeau D, Gaumont A.-C. J. Org. Chem. 2003; 68: 7016
- 7b Guenin E, Meziane D. Curr. Org. Chem. 2011; 15: 3465
- 7c Keglevich G, Bálint E, Takács J, Drahos L, Huben K, Jankowski S. Curr. Org. Synth. 2014; 11: 161
- 8 Alonso F, Moglie Y, Radivoy G, Yus M. Green Chem. 2012; 14: 2699
- 9 Malysheva SF, Gusarova NK, Artem’ev AV, Belogorlova NA, Albanov AI, Borodina TN, Smirnov VI, Trofimov BA. Eur. J. Org. Chem. 2014; 2516
- 10a Gusarova NK, Bogdanova MV, Ivanova NI, Chernysheva NA, Sukhov BG, Sinegovskaya LM, Kazheva ON, Alexandrov GG, Dyachenko OA, Trofimov BA. Synthesis 2005; 3103
- 10b 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
- 10c Malysheva SF, Artem’ev AV, Gusarova NK, Timokhin BV, Tatarinova AA, Trofimov BA. Russ. J. Gen. Chem. 2009; 79: 1617
- 11 Trofimov BA, Malysheva SF, Gusarova NK, Belogorlova NA, Vasilevsky SF, Kobychev VB, Sukhov BG, Ushakov IA. Mendeleev Commun. 2007; 17: 181
- 12 Trofimov BA, Gusarova NK, Arbuzova SN, Ivanova NI, Artem’ev AV, Volkov PA, Ushakov IA, Malysheva SF, Kuimov VA. J. Organomet. Chem. 2009; 694: 677
- 13 Gusarova NK, Malysheva SF, Belogorlova NA, Kuimov VA, Ushakov IA, Trofimov BA. Russ. Chem. Bull. 2009; 58: 234
- 14 Arbuzova SN, Gusarova NK, Bogdanova MV, Ivanova NI, Ushakov IA, Mal’kina AG, Trofimov BA. Mendeleev Commun. 2005; 15: 183
- 15 Arbuzova SN, Gusarova NK, Bogdanova MV, Ivanova NI, Ushakov IA, Mal’kina AG, Trofimov BA. Mendeleev Commun. 2007; 17: 325
- 16 Glotova TE, Dvorko MYu, Gusarova NK, Arbuzova SN, Ushakov IA, Kazantseva TI, Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 1396
- 17 Li J.-N, Liu L, Fu Y, Guo Q.-X. Tetrahedron 2006; 62: 4453
- 18 Trofimov BA, Artem’ev AV, Malysheva SF, Gusarova NK. Dokl. Chem. 2009; 428: 225
- 19 Becke AD. J. Chem. Phys. 1993; 98: 5648
- 20 For example, see: Allefeld N, Grasse M, Ignat’ev N, Hoge B. Chem. Eur. J. 2014; 20: 8615
- 21 Trofimov BA, Brandsma L, Arbuzova SN, Malysheva SF, Gusarova NK. Tetrahedron Lett. 1994; 35: 7647
For selected reviews, see: