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
Synlett 2015; 26(07): 980-984
DOI: 10.1055/s-0034-1380326
DOI: 10.1055/s-0034-1380326
letter
Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C−C Cross-Coupling Reactions of (1-Halovinyl)phosphonates
Further Information
Publication History
Received: 30 December 2014
Accepted: 19 January 2015
Publication Date:
20 February 2015 (online)
Abstract
An efficient new synthetic route to (1-arylvinyl)phosphonates is presented. A wide range of (1-arylvinyl)phosphonates were prepared in good to excellent yields (79–99%) by using a palladium(II) acetate–organophosphine catalyst system. The protocol can be effectively scaled up without deleterious effects. The use of a (1-chlorovinyl)phosphonate as the electrophilic coupling partner was demonstrated for the first time.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380326.
- Supporting Information
-
References and Notes
- 1a Iorga B, Eymery F, Carmichael D, Savignac P. Eur. J. Org. Chem. 2000; 3103
- 1b Wang H.-Q, Liu Z.-J. Youji Huaxue 2003; 23: 321 ; Chem. Abstr. 2003, 139, 338028
- 1c Wang D.-Y, Hu X.-P, Deng J, Yu S.-B, Duan Z.-C, Zheng Z. J. Org. Chem. 2009; 74: 4408
- 1d Dong K, Wang Z, Ding K. J. Am. Chem. Soc. 2012; 134: 12474
- 1e Goulioukina NS, Dolgina TM, Bondarenko GN, Beletskaya IP, Ilyin MM, Davankov VA, Pfaltz A. Tetrahedron: Asymmetry 2003; 14: 1397
- 2a Sobhani S, Honarmand M. Synlett 2013; 24: 236
- 2b Li S.-N, Xu L.-T, Chen Y, Li J.-L, He L. Lett. Org. Chem. 2011; 8: 416
- 2c Krawczyk H, Koszuk J, Bodalski R. Pol. J. Chem. 2000; 74: 1123
- 2d Yamashita M, Kojima M, Yoshida H, Ogata T, Inokawa S. Bull. Chem. Soc. Jpn. 1980; 53: 1625
- 2e Axelrad G, Laosooksathit S, Engel R. J. Org. Chem. 1981; 46: 5200
- 3 Yang L, Qi X, Xu L. Huaxue Jinzhan 2011; 23: 893 ; Chem. Abstr. 2011, 155, 123466
- 4a Han L.-B, Tanaka M. J. Am. Chem. Soc. 1996; 118: 1571
- 4b Han L.-B, Zhang C, Yazawa H, Shimada S. J. Am. Chem. Soc. 2004; 126: 5080
- 4c Xu Q, Shen R, Ono Y, Nagahata R, Shimada S, Goto M, Han L.-B. Chem. Commun. 2011; 47: 2333
- 4d Xu Q, Zhao C, Zhou Y, Yin S, Han L. Youji Huaxue 2012; 32: 1761 ; Chem. Abstr. 2012, 158, 216049
- 5a Goulioukina NS, Dolgina TM, Beletskaya IP, Henry J.-C, Lavergne D, Ratovelomanana-Vidal V, Genet J.-P. Tetrahedron: Asymmetry 2001; 12: 319
- 5b Gulykina NS, Dolgina TM, Bondarenko GN, Beletskaya IP. Russ. J. Org. Chem. 2003; 39: 797
- 5c Ananikov VP, Khemchyan LL, Beletskaya IP, Starikova ZA. Adv. Synth. Catal. 2010; 352: 2979
- 5d Trostyanskaya IG, Beletskaya IP. Tetrahedron 2014; 70: 2556
- 5e Khemchyan LL, Ivanova JV, Zalesskiy SS, Ananikov VP, Beletskaya IP, Starikova ZA. Adv. Synth. Catal. 2014; 356: 771
- 6 Kalek M, Ziadi A, Stawinski J. Org. Lett. 2008; 10: 4637
- 7 Andaloussi M, Lindh J, Sävmarker J, Sjöberg PJ. R, Larhed M. Chem. Eur. J. 2009; 15: 13069
- 8a Pergament I, Srebnik M. Org. Lett. 2001; 3: 217
- 8b Kobayashi Y, William AD. Org. Lett. 2002; 4: 4241
- 8c Kobayashi Y, William AD. Adv. Synth. Catal. 2004; 346: 1749
- 8d Pergament I, Srebnik M. Tetrahedron Lett. 2001; 42: 8059
- 9a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 9b Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
- 9c Lennox AJ. J, Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412
- 9d Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 10a Liu Y, Fang Y, Zhang L, Jin X, Li R, Zhu S, Gao H, Fang J, Xia Q. Youji Huaxue 2014; 34: 1523
- 10b Yang J, Zhang L, Jin X, Gao H, Fang J, Li R, Fang Y. Youji Huaxue 2013; 33: 1647 ; Chem. Abstr. 2014, 160, 606233
- 10c Jin X, Zhang L, Gao H, Fang J, Li R, Fang Y. Huaxue Jinzhan 2013; 25: 1898
- 11a Doğan Ö, Isci M, Aygun M. Tetrahedron: Asymmetry 2013; 24: 562
- 11b Doğan Ö, Babiz H, Gözen AG, Budak S. Eur. J. Med. Chem. 2011; 46: 2485
- 12a Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
- 12b Billingsley K, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3358
- 14 Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
- 15 Kobayashi Y, Mizojiri R, Ikeda E. J. Org. Chem. 1996; 61: 5391
- 16 Diethyl [1-(2-Tolyl)vinyl]phosphonate (3b); Typical Procedure A Schlenk flask was charged with phosphonate 2a (97.2 mg, 0.4 mmol), Pd(OAc)2 (4.5 mg, 0.02 mmol), t-Bu3P∙HBF4 (11.6 mg, 0.04 mmol), 2-TolB(OH)2 (81.6 mg, 0.6 mmol), and K2CO3 (138.0 mg, 1.0 mmol). The flask was evacuated for 10 min and then filled with N2. Toluene (2.0 mL) was added, and the mixture was stirred at r.t. for 10 h. When the reaction as complete, the mixture was diluted with EtOAc (15.0 mL) and the catalyst and inorganic base were removed by filtration through a short pad of silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography [silica gel, PE–EtOAc (2:1)] to give a pale-yellow oil; yield: 92.5 mg (91%); IR (KBr): 3450, 2983, 2928, 1489, 1392, 1256, 1234, 1022, 962 cm–1; 1H NMR (500 MHz, CDCl3): δ = 1.27 (t, J = 7.0 Hz, 6 H), 2.31 (s, 3 H), 4.04–4.10 (m, 4 H), 5.84 (dd, J = 2.0, 47.7 Hz, 1 H), 6.42 (dd, J = 22.6, 2.0 Hz, 1 H), 7.13–7.17 (m, 2 H), 7.20–7.21 (m, 2 H); 13C NMR (125 MHz, CDCl3): δ = 16.3 (d, J = 6.4 Hz), 20.0, 62.2 (d, J = 6.1 Hz), 125.3 (d, J = 1.5 Hz), 127.8 (d, J = 1.8 Hz), 129.1 (d, J = 3.6 Hz), 130.2, 133.0 (d, J = 8.5 Hz), 136.0 (d, J = 5.4 Hz), 136.6 (d, J = 9.4 Hz), 140.0 (J = 175.8 Hz); 31P NMR (202.5 MHz, CDCl3): δ = 16.0; GC/MS: m/z (%) 254 (27) [M+], 226 (11), 197 (48), 179 (5), 144 (4), 115 (100), 91 (12), 65 (8); HRMS (ESI): m/z [M + Na+] calcd for C13H19NaO3P: 277.0970; found: 277.1004.
For selected reviews, see: