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 2017; 49(21): 4783-4807
DOI: 10.1055/s-0036-1588542
DOI: 10.1055/s-0036-1588542
short review
Catalyst- and Solvent-Free Addition of the P–H Species to Alkenes and Alkynes: A Green Methodology for C–P Bond Formation
This study was performed under financial support by the Council for Grants at the President of the Russian Federation (project no. NSh-7145.2016.3).Further Information
Publication History
Received: 25 May 2017
Accepted after revision: 18 July 2017
Publication Date:
28 August 2017 (online)
Abstract
Traditional methods for C–P bond formation via direct addition of P–H species to unsaturated compounds are usually implemented in the presence of base and metal catalysts or radical initiators in various organic solvents. During the last five years, a novel efficient and general catalyst/initiator- and solvent-free version of the hydrophosphination and hydrophosphinylation of multiple C–C bonds with H-phosphines and their chalcogenides has begun to develop and it is attracting growing attention. This approach corresponds to the recently emerged pot-, atom-, and step-economy (PASE) green paradigm. This review covers the literature on the synthesis of useful and in-demand organophosphorus compounds via catalyst- and solvent-free addition of P–H species to alkenes and alkynes.
1 Introduction
2 Addition of Secondary Phosphines to Alkenes
3 Hydrophosphinylation of Alkenes with Secondary Phosphine Chalcogenides
3.1 Oxidative Addition of Phosphine Oxides to Vinyl Sulfides
3.2 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Alkenes
3.3 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Divinyl Chalcogenides
3.4 Hydrophosphinylation of Alkenes with Secondary Phosphine/Chalcogen Pair (Three-Component Reactions)
4 Addition of Secondary Phosphines to Alkynes
5 Addition of Secondary Phosphine Chalcogenides to Alkynes
6 Conclusion
-
References
- 1a Baillie C. Xiao J. Curr. Org. Chem. 2003; 7: 477
- 1b Alonso F. Beletskaya IP. Yus M. Chem. Rev. 2004; 104: 3079
- 1c Delacroix O. Gaumont AC. Curr. Org. Chem. 2005; 9: 1851
- 1d Leca D. Fensterbank L. Lacôte E. Malacria M. Chem. Soc. Rev. 2005; 34: 858
- 1e Arbuzova SN. Gusarova NK. Trofimov BA. ARKIVOC 2006; (v): 12
- 1f Honaker MT. Hovland JM. Salvatore RN. Curr. Org. Synth. 2007; 4: 31
- 1g Coudray L. Montchamp J.-L. Eur. J. Org. Chem. 2008; 3601
- 1h Ananikov VP. Khemchyan LL. Beletskaya IP. Synlett 2009; 2375
- 1i Glueck DS. Top. Organomet. Chem. 2010; 31: 65
- 1j Gusarova NK. Arbuzova SN. Trofimov BA. Pure Appl. Chem. 2012; 84: 439
- 2a Bunlaksananusorn T. Knochel P. Tetrahedron Lett. 2002; 43: 5817
- 2b Gusarova NK. Bogdanova MV. Ivanova NI. Chernysheva NA. Sukhov BG. Sinegovskaya LM. Kazheva ON. Alexandrov GG. D’yachenko OA. Trofimov BA. Synthesis 2005; 3103
- 2c Greenberg S. Gibson GL. Stephan DW. Chem. Commun. 2009; 304
- 3a Kazankova MA. Shulyupin MO. Beletskaya IP. Synlett 2003; 2155
- 3b Scriban C. Glueck DS. Zakharov LN. Scott Kassel W. DiPasquale AG. Golen JA. Rheingold AL. Organometallics 2006; 25: 5757
- 3c Arisawa M. Yamaguchi M. Tetrahedron Lett. 2009; 50: 45
- 3d Leyva-Pérez A. Vidal-Moya JA. Cabrero-Antonino JR. Al-Deyab SS. Al-Resayes SI. Corma A. J. Organomet. Chem. 2011; 696: 362
- 3e Xu C. Kennard GJ. H. Hennersdorf F. Li Y. Pullarkat SA. Leung P.-H. Organometallics 2012; 31: 3022
- 3f Liu B. Roisnel T. Carpentier J.-F. Sarazin Y. Chem.–Eur. J. 2013; 19: 13445
- 3g Pullarkat SA. Leung P.-H. Top. Organomet. Chem. 2013; 43: 145
- 3h Hayashi M. Matsuura T. Tanaka I. Ohta H. Watanabe Y. Org. Lett. 2013; 15: 628
- 3i Routaboul L. Toulgoat F. Gatignol J. Lohier J.-F. Norah B. Delacroix O. Alayrac C. Taillefer M. Gaumond A.-C. Chem.–Eur. J. 2013; 19: 8760
- 3j Koshti V. Gaikwad S. Chikkali SH. Coord. Chem. Rev. 2014; 265: 52
- 3k Basalov IV. Rosca SC. Lyubov DM. Selikhov AN. Fukin GK. Sarazin Y. Carpentier J.-F. Trifonov AA. Inorg. Chem. 2014; 53: 1654
- 3l Rosca S.-C. Roisnel T. Dorcet V. Carpentier J.-F. Sarazin Y. Organometallics 2014; 33: 5630
- 3m Gallager KJ. Webster RL. Chem. Commun. 2014; 50: 12109
- 3n Gutiérrez V. Mascaró E. Alonso F. Moglie Y. Radivoy G. RSC Adv. 2015; 5: 65739
- 4a Quin LD. A Guide to Organophosphorus Chemistry . John Wiley; New York: 2000: 28-29
- 4b Parsons AF. Sharpe DJ. Taylor P. Synlett 2005; 2981
- 4c Jessop CM. Parsons AF. Routledge A. Irvine DJ. Eur. J. Org. Chem. 2006; 1547
- 4d Gusarova NK. Chernysheva NA. Yas’ko SV. Kazantseva TI. Ushakov IA. Trofimov BA. Synthesis 2008; 2743
- 4e Gusarova NK. Malysheva SF. Belogorlova NA. Parshina LN. Trofimov BA. Synthesis 2011; 1777
- 4f Oparina LA. Gusarova NK. Vysotskaya OV. Artem’ev AV. Kolyvanov NA. Trofimov BA. Synthesis 2014; 46: 653
- 5a Cantat T. Mezailles N. Ricard L. Jean Y. Le Floch P. Angew. Chem. Int Ed. 2004; 43: 6382
- 5b Imamoto T. Oohara N. Takahashi H. Synthesis 2004; 1353
- 5c Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications. Börner A. Wiley-VCH; Weinheim: 2008
- 5d Goudriann PE. van Leeuwen PW. N. M. Birkholz M.-N. Reek JN. H. Eur. J. Org. Chem. 2008; 2939
- 5e Lühr S. Holz J. Börner A. ChemCatChem 2011; 3: 1708
- 5f Fernández-Pérez H. Etayo P. Panossian A. Vidal-Ferran A. Chem. Rev. 2011; 111: 2119
- 5g Privileged Chiral Ligands and Catalysis . Zhou Q.-L. Wiley-VCH; Weinheim: 2011
- 5h Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis . Kamer PC. J. van Leeuwen PW. N. M. John Wiley; Chichester: 2012
- 5i Fan YC. Kwon O. Chem. Commun. 2013; 49: 11588
- 5j Aizawa S. Fukumoto K. Kawamoto T. Polyhedron 2013; 62: 37
- 5k Canales S. Villacampa MD. Laguna A. Gimeno MC. J. Organomet. Chem. 2014; 760: 84
- 5l Xiao Y. Guo H. Kwon O. Aldrichim. Acta 2016; 49: 3
- 6a Mayhew DL. Clive DL. J. Triphenylphosphine Sulfide. In e-EROS Encyclopedia of Reagents for Organic Synthesis [Online]. Wiley-VCH; 2001. DOI: 10.1002/047084289X.rt379
- 6b Chapman CJ. Frost CG. Gill-Carey MP. Kociok-Köhn G. Mahon MF. Weller AS. Willis MC. Tetrahedron: Asymmetry 2003; 14: 705
- 6c Ichikawa E. Suzuki M. Yabu K. Albert M. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2004; 126: 11808
- 6d Ono Y. Han L.-B. Tetrahedron Lett. 2006; 47: 421
- 6e Gaumont AC. Gulea M. Science of Synthesis . Vol. 33. Thieme; Stuttgart: 2007: 665-694 and 701-710
- 6f Gonzalez-Nogal AM. Cuadrado P. Sarmentero MA. Tetrahedron 2010; 66: 9610
- 6g Boercker JE. Foos EE. Placencia D. Tischler JG. J. Am. Chem. Soc. 2013; 135: 15071
- 6h García-Rodríguez R. Liu H. J. Am. Chem. Soc. 2014; 136: 1968
- 7a Alonso F. Moglie Y. Radivoy G. Yus M. Green Chem. 2012; 14: 2699
- 7b Alonso F. Moglie Y. Curr. Green Chem. 2014; 1: 87
- 7c Malysheva SF. Gusarova NK. Artem’ev AV. Belogorlova NA. Albanov AI. Borodina TN. Smirnov VI. Trofimov BA. Eur. J. Org. Chem. 2014; 2516
- 7d Malysheva SF. Gusarova NK. Artem’ev AV. Belogorlova NA. Albanov AI. Borodina TN. Smirnov VI. Trofimov BA. Synthesis 2014; 46: 2656
- 7e Malysheva SF. Artem’ev AV. Gusarova NK. Belogorlova NA. Albanov AI. Liu CW. Trofimov BA. Beilstein J. Org. Chem. 2015; 11: 1985
- 7f Gusarova NK. Chernysheva NA. Yas’ko SV. Trofimov BA. J. Sulfur Chem. 2015; 36: 526
- 7g Artem’ev AV. Malysheva SF. Gusarova NK. Belogorlova NA. Shagun VA. Albanov AI. Trofimov BA. Synthesis 2015; 47: 263
- 7h Gusarova NK. Ivanova NI. Volkov PA. Khrapova KO. Larina LI. Smirnov VI. Borodina TN. Trofimov BA. Synthesis 2015; 47: 1611
- 7i Moglie Y. González-Soria MJ. Martín-García I. Radivoy G. Alonso F. Green Chem. 2016; 18: 4896
- 7j Gusarova NK. Chernysheva NA. Yas’ko SV. Klyba LV. Trofimov BA. J. Sulfur Chem. 2016; 37: 488
- 7k Artem’ev AV. Chernysheva NA. Yas’ko SV. Gusarova NK. Bagryanskaya IYu. Trofimov BA. Heteroatom Chem. 2016; 27: 48
- 7l Chernysheva NA. Yas’ko SV. Gusarova NK. Trofimov BA. Russ. J. Org. Chem. 2016; 52: 1511
- 8a Fu X. Jiang Z. Tan C.-H. Chem. Commun. 2007; 5058
- 8b Perrier A. Comte V. Moïse C. Richard P. Le Gendre P. Eur. J. Org. Chem. 2010; 1562
- 9a Shulyupin MO. Kazankova MA. Beletskaya IP. Org. Lett. 2002; 4: 761
- 9b Xu Q. Han L.-B. J. Organomet. Chem. 2011; 696: 130
- 9c Tanaka M. Top. Organomet. Chem. 2013; 43: 167
- 10a Guo R. Li X. Wu J. Kwok WH. Chen J. Choi MC. K. Chan AS. C. Tetrahedron Lett. 2002; 43: 6803
- 10b Trofimov BA. Gusarova NK. Malysheva SF. Ivanova NI. Sukhov BG. Belogorlova NA. Kuimov VA. Synthesis 2002; 2207
- 10c Trofimov BA. Gusarova NK. Sukhov BG. Malysheva SF. Tarasova OA. Belogorlova NA. Maximova MA. Tunik SP. Synthesis 2005; 965
- 11a Dombek BD. J. Org. Chem. 1978; 43: 3408
- 11b Malysheva SF. Gusarova NK. Belogorlova NA. Nikitin MV. Gendin DV. Trofimov BA. Russ. J. Gen. Chem. 1997; 67: 58
- 12a Lobana TS. Mahajan P. Pannu AS. Hundal G. Butcher RJ. J. Coord. Chem. 2007; 60: 733
- 12b Kilpin KJ. Henderson W. Nicholson K. Dalton Trans. 2010; 39: 1855
- 12c Pop A. Silvestru A. Gimeno MC. Laguna A. Kulcsar M. Arca M. Lippolis V. Pintus A. Dalton Trans. 2011; 40: 12479
- 13 Selenium: Its Molecular Biology and Role in Human Health . 3rd ed.; Hatfield DL. Berry MJ. Gladyshev VN. Springer; New York: 2012
- 14a Koh W. Yoon Y. Murray CB. Chem. Mater. 2011; 23: 1825
- 14b Vaughn DD. In S.-l. Schaak RE. ACS Nano 2011; 5: 8852
- 15 Hirai T. Han L.-B. Org. Lett. 2007; 9: 53
- 16a Subasi E. Senturk OS. Ugur F. Z. Naturforsch., B 2004; 59: 836
- 16b Aizawa S. Tamai M. Sakuma M. Kubo A. Chem. Lett. 2007; 36: 130
- 16c Dutta DK. Deb B. Coord. Chem. Rev. 2011; 255: 1686
- 16d Chatterjee S. Patel SK. Tirkey V. Mobin SM. J. Organomet. Chem. 2012; 699: 12
- 16e Persson R. Stchedroff MJ. Gobetto R. Carrano CJ. Richmond MG. Monari M. Nordlander E. Eur. J. Inorg. Chem. 2013; 2013: 2447
- 16f Mottalib MA. Haukka M. Nordlander E. Polyhedron 2016; 103: 275
- 17a Rackham O. Nichols SJ. Leedman PJ. Berners-Price SJ. Filipovska A. Biochem. Pharmacol. 2007; 74: 992
- 17b Tian S. Siu FM. Kiu SC. F. Lok CN. Che CM. Chem. Commun. 2011; 47: 9318
- 17c Wetzel C. Kunz PC. Kassack MU. Hamacher A. Böhler P. Watjen W. Ott I. Rubbiani R. Spingler B. Dalton Trans. 2011; 40: 9212
- 17d Khalladi K. Touil S. J. Sulfur Chem. 2012; 33: 27
- 17e Elkhaldy AA. S. Hussien AR. Abu Shanab AM. Wassef MA. J. Sulfur Chem. 2012; 33: 295
- 18a Belletti D. Graiff C. Lostao V. Pattacini R. Predieri G. Tiripicchio A. Inorg. Chim. Acta. 2003; 347: 137
- 18b Sashchiuk A. Amirav L. Bashouti M. Krueger M. Sivan U. Lifshitz E. Nano Lett. 2004; 4: 159
- 18c Snee PT. Somers RC. Nair G. Zimmer JP. Bawendi MG. Nocera DG. J. Am. Chem. Soc. 2006; 128: 13320
- 18d Liu H. Owen JS. Alivisatos AP. J. Am. Chem. Soc. 2007; 129: 305
- 19a Clarke PA. Santos S. Martin WH. C. Green Chem. 2007; 9: 438
- 19b Vereshchagin AN. Elinson MN. Anisina YuE. Ryzhkov FV. Goloveshkin AS. Bushmarinov IS. Zlotin SG. Egorov MP. Mendeleev Commun. 2015; 25: 424
- 20a Kazankova MA. Efimova IV. Kochetkov AN. Afanas’ev VV. Beletskaya IP. Russ. J. Org. Chem. 2002; 38: 1465
- 20b Hu H. Cui C. Organometallics 2012; 31: 1208
- 20c Takaki K. Koshoji G. Komeyama K. Takeda M. Shishido T. Kitani A. Takehira K. J. Org. Chem. 2003; 68: 6554
- 20d Join B. Mimeau D. Delacroix O. Gaumont A.-C. Chem. Commun. 2006; 3249
- 20e Kondoh A. Yorimitsu H. Oshima K. J. Am. Chem. Soc. 2007; 129: 4099
- 20f Al-Shboul TM. A. Pálfi VK. Yu L. Kretschmer R. Wimmer K. Fischer R. Görls H. Reiher M. Westerhausen M. J. Organomet. Chem. 2011; 696: 216
- 20g Kamitami M. Itazaki M. Tamiya C. Nakazawa H. J. Am. Chem. Soc. 2012; 134: 11932
- 20h Kissel AA. Mahrova TV. Lyubov DM. Cherkasov AV. Fukin GK. Trifonov AA. Del Rosal I. Maron L. Dalton Trans. 2015; 44: 12137
- 21a Kostyanovsky RG. El’natanov YuI. Izv. Akad. Nauk SSSR, Ser. Khim. 1983; 2581
- 21b El’natanov YuI. Kostyanovsky RG. Izv. Akad. Nauk SSSR, Ser. Khim. 1988; 382
- 21c Trofimov BA. Arbuzova SN. Mal’kina AG. Gusarova NK. Malysheva SF. Nikitin MV. Vakul’skaya TI. Mendeleev Commun. 1999; 9: 163
- 21d Gusarova NK. Shaikhudinova SI. Arbuzova SN. Vakul’skaya TI. Sukhov BG. Sinegovskaya LM. Nikitin MV. Mal’kina AG. Chernysheva NA. Trofimov BA. Tetrahedron 2003; 59: 4789
- 22a Khachatryan RA. Grigoryan NY. Indzhikyan MG. Zh. Obshch. Khim. 1994; 64: 1260 ; Chem. Abstr. 1995, 122, 290971
- 22b Arbuzova SN. Gusarova NK. Bogdanova MV. Ivanova NI. Ushakov IA. Mal’kina AG. Trofimov BA. Mendeleev Commun. 2005; 15: 183
- 22c Glotova TE. Dvorko MYu. Arbuzova SN. Ushakov IA. Verkhoturova SI. Gusarova NK. Trofimov BA. Lett. Org. Chem. 2007; 4: 109
- 22d Glotova TE. Dvorko MYu. Gusarova NK. Arbuzova SN. Ushakov IA. Kazantseva TI. Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 1396
- 23 Trofimov BA. Malysheva SF. Gusarova NK. Belogorlova NA. Vasilevsky SF. Kobychev VB. Sukhov BG. Ushakov IA. Mendeleev Commun. 2007; 17: 181
- 24 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
For reviews, see: