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-00000083.xml
Download PDF
Synlett 2014; 25(19): 2727-2732
DOI: 10.1055/s-0034-1379545
DOI: 10.1055/s-0034-1379545
cluster
Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkenes in the Synthesis of Alkenylphosphine Oxides
Authors
Further Information
Publication History
Received: 11 September 2014
Accepted after revision: 30 October 2014
Publication Date:
06 November 2014 (online)
Abstract
The first copper-catalyzed alkene oxidative cross-coupling reaction with various R2P(O)H compounds has been reported, affording a novel and efficient method for the synthesis of valuable alkenylphosphine oxides compounds with broad substrate applicability and succinct reaction system with immoderate to good yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000083.
- (PDF)
-
References and Notes
- 1a Zhao D.-P, Wang R. Chem. Soc. Rev. 2012; 41: 2095
- 1b Li Y, Josowicz M, Tolbert L.-M. J. Am. Chem. Soc. 2012; 132: 10374
- 1c Zhou A.-X, Mao L.-L, Wang G.-W, Yang S.-D. Chem. Commun. 2014; 50: 8529
Reference Ris Wihthout Link
- 1d Alexandre F.-R, Amador A, Bot S, Caillet C, Convard T, Jakubik J, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Roland A, Seifer M, Standring D, Storer R, Dousson C.-B. J. Med. Chem. 2011; 54: 392
- 2a Bialy L, Waldmann H. Angew. Chem. Int. Ed. 2005; 44: 3814
- 2b George A, Veis A. Chem. Rev. 2008; 108: 4670
- 2c Nicolaou KC, Maligres P, Shin J, Leon E, Rideouts D. J. Am. Chem. Soc. 1990; 112: 1826
- 2d Haynes RK, Loughlin WA, Hambley TW. J. Org. Chem. 1991; 56: 5785
- 2e Haynes RK, Vonwiller SC, Hambley TW. J. Org. Chem. 1989; 54: 5162
- 3a Grushin VV. Chem. Rev. 2004; 104: 1629
- 3b Fernández-Pérez H, Etayo P, Panossian A, Vidal-Ferran A. Chem. Rev. 2011; 111: 2119
- 3c Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
- 3d Coote SC, Bach T. J. Am. Chem. Soc. 2013; 135: 14948
- 3e Inoue H, Nagaoka Y, Tomioka K. J. Org. Chem. 2002; 67: 5864
- 4a Brunner H, Courcy NL. C, Genêt J.-P. Synlett 2000; 201
- 4b Burini A, Cacchi S, Pace P, Pietroni BR. Synlett 1995; 677
- 4c Kabalka GW, Guchhait SK, Naravane A. Tetrahedron Lett. 2004; 45: 4685
- 4d Jouvin K, Coste A, Bayle A, Legrand F, Karthikeyan G, Tadiparthi K, Evano G. Organometallics 2012; 31: 7933
- 4e Uozumi Y, Kimura T. Synlett 2002; 2045
- 4f Al-Maksoud W, Mesnager J, Jaber F, Pinel C, Djakovitch L. J. Organomet. Chem. 2009; 694: 3222
- 5a Hu J, Zhao N, Yang B, Wang Ge, Guo L.-N, Liang Y.-M, Yang S.-D. Chem. Eur. J. 2011; 17: 5516
- 5b Li X, Yang F, Wu Y, Wu Y. Org. Lett. 2014; 16: 992
Reference Ris Wihthout Link
- 5c Hu G.-B, Gao Y.-X, Zhao Y.-F. Org. Lett. 2014; 16: 4464
Reference Ris Wihthout Link
- 5d Wu Y.-L, Liu L, Yan K.-L, Xu P.-X, Gao Y.-X, Zhao Y.-F. J. Org. Chem. 2014; 79: 8118
Reference Ris Wihthout Link
- 6a Pergament I, Srebnik M. Tetrahedron Lett. 2001; 42: 8059
- 6b Pergament I, Srebnik M. Org. Lett. 2001; 3: 217
- 6c Evano G, Tadiparthi K, Couty F. Chem. Commun. 2011; 47: 179
- 6d Thielges S, Bisseret P, Eustache J. Org. Lett. 2005; 7: 681
- 6e Jouvin K, Coste A, Bayle A, Legrand F, Karthikeyan G, Tadiparthi K, Evano G. Organometallics 2012; 31: 7933
- 6f Liu L, Wang Y.-L, Zeng Z.-P, Xu P.-X, Gao Y.-X, Yin Y.-W, Zhao Y.-F. Adv. Synth. Catal. 2013; 355: 659
Reference Ris Wihthout Link
- 6g Xu Y.-Y, Xia J.-Z, Guo H.-J. Synthesis 1986; 691
- 7a Han L.-B, Zhang C, Yazawa H, Shimada S. J. Am. Chem. Soc. 2004; 126: 5080
Reference Ris Wihthout Link
- 7b Han L.-B, Hua R, Tanaka M. Angew. Chem. Int. Ed. 1998; 37: 1
- 7c Takaki K, Takeda M, Koshoji G, Shishido T, Takehira K. Tetrahedron Lett. 2001; 6357
- 7d Takaki K, Koshoji G, Komeyama K, Takeda M, Shishido T, Kitani A, Takehira K. J. Org. Chem. 2003; 68: 6554
- 7e Niu M.-Y, Fu H, Jiang Y.-Y, Zhao Y.-F. Chem. Commun. 2007; 272
- 7f Trostyanskaya IG, Beletskaya IP. Tetrahedron 2014; 70: 2556
Reference Ris Wihthout Link
- 7g Han L.-B, Zhao C.-Q, Tanaka M. J. Org. Chem. 2001; 66: 5929
Reference Ris Wihthout Link
- 8a Kouno R, Okauchi T, Nakamura M, Ichikawa J, Minami T. J. Org. Chem. 1998; 63: 6239
- 8b Shen Y, Jiang G.-F. Synthesis 2000; 99
- 8c Lee H.-S, Lim C.-H, Lee H.-J, Kim J.-N. Bull. Korean Chem. Soc. 2012; 33: 3817
- 8d Alves D, Schumacher RF, Brandão R, Nogueira CW, Zeni G. Synlett 2006; 1035
- 8e Nishimura T, Hirabayashi S, Yasuhara Y, Hayash T. J. Am. Chem. Soc. 2006; 128: 2556
- 9a Rauf W, Brown JM. Chem. Commun. 2013; 49: 8430
- 9b Cartney DM, Guiry PJ. Chem. Soc. Rev. 2011; 40: 5122
- 9c Zhou L.-H, Lu W.-J. Chem. Eur. J. 2014; 20: 634
- 9d Yu Y.-Y, Niphakis M.-J, Georg G.-I. Org. Lett. 2011; 13: 5932
- 10a Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
- 10b Wu Y, Wang J, Mao F, Kwong F.-Y. Chem. Asian J. 2014; 9: 26
- 10c Zhou L.-H, Lu W.-J. Chemistry 2014; 20: 634
- 10d Graczyk K, Ma W, Ackermann L. Org. Lett. 2012; 14: 4110
- 10e Nishikata T, Lipshutz BH. Org. Lett. 2010; 12: 1972
- 10f Liu X.-Z, Hii K.-K. J. Org. Chem. 2011; 76: 8022
- 11a Molander GA, Romero JA. C. Chem. Rev. 2002; 102: 2161
- 11b Han L.-B, Zhao C.-Q. J. Org. Chem. 2005; 70: 10121
- 11c Leyva-Pérez A, Vidal-Moya JA, Cabrero-Antonino JR, Al-Deyab SS, Al-Resayes SI, Corma A. J. Organomet. Chem. 2011; 696: 362
- 11d Isley NA, Linstadt RT. H, Slack ED, Lipshutz BH. Dalton Trans. 2014; 43: 13196
- 11e Ortial S, Fisher HC, Montchamp J.-L. J. Org. Chem. 2013; 78: 6599
Reference Ris Wihthout Link
- 11f Stockland RA. Jr, Taylor R.-I, Thompson LE, Patel PB. Org. Lett. 2005; 7: 851
- 12a Li Y.-M, Sun M, Wang H.-L, Tian Q.-P, Yang S.-D. Angew.Chem. Int. Ed. 2013; 52: 3972
- 12b Li Y.-M, Yang S.-D. Synlett 2013; 24: 1739
- 12c Zhang H.-Y, Sun M, Ma Y.-N, Tian Q.-P, Yang SD. Org. Biomol. Chem. 2012; 10: 9627
- 12d Yang B, Yang T.-T, Li X.-A, Wang J.-J, Yang S.-D. Org. Lett. 2013; 15: 5024
- 12e Sun M, Zhang H.-Y, Han Q, Yang K, Yang S.-D. Chem. Eur. J. 2011; 17: 9566
- 12f Zhou A.-X, Mao L.-L, Wang GW, Yang S.-D. Chem. Commun. 2014; 50: 8529
Reference Ris Wihthout Link
- 12g Yang B, Tian Q.-P, Yang S.-D. Chin. J. Org. Chem. 2014; 34: 717
- 13a Li C.-J. Acc. Chem. Res. 2009; 42: 335
Reference Ris Wihthout Link
- 13b Janes R, Symons MC. R. J. Chem. Soc., Faraday Trans. 1990; 86: 2173
- 13c Waal BF. M, Aagaard O.-M, Janssen RA. J. J. Am. Chem. Soc. 1991; 113: 9471
- 13d Li Z.-J, Fan F.-H, Yang J, Liu Z.-Q. Org. Lett. 2014; 16: 3396
- 14 Typical Procedure of Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkene to Synthesize Alkenylphosphine Oxides In a reaction tube, dicumyl peroxide (0.6 mmol, 2.0 equiv) and CuCl2·2H2O (0.03 mmol, 10 mol%), H(O)PPh2 (0.30 mmol) were added and charged with Ar three times. Then, 1,1-diphenylethylene (0.90 mmol) and MeCN (3 mL) were added. The mixture was stirred at 80 °C for 12 h. After completion of the reaction, the solvent was distilled under rotary evaporation. The crude product was purified by flash chromatography on silica gel to give the desired products (PE–EtOAc, 1:1), yielding (2,2-diphenylvinyl)diphenyl-phosphine oxide as white solid (97 mg, 84%). 1H NMR (400 MHz, CDCl3): δ = 7.76–7.60 (m, 4 H), 7.47–7.27 (m, 11 H), 7.23 (d, J = 6.8 Hz, 2 H), 7.17–7.03 (m, 3 H), 6.79 (d, J = 18.2 Hz, 1 H). 13C NMR (101 MHz, CDCl3): δ = 161.88, 161.85, 141.87, 141.71, 137.94, 137.87, 134.29 (d, J = 105.9 Hz), 130.96, 130.94, 130.80, 130.71, 130.20, 129.41, 128.52, 128.26, 128.21, 128.18, 128.09, 127.47, 120.45 (d, J = 103.7 Hz). 31P NMR (162 MHz, CDCl3): δ = 18.74. ESI-MS: m/z [M + H]: 381.1407.