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(01): 71-78
DOI: 10.1055/s-0034-1379163
DOI: 10.1055/s-0034-1379163
paper
Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate
Further Information
Publication History
Received: 28 May 2014
Accepted after revision: 26 August 2014
Publication Date:
25 September 2014 (online)
Abstract
The commercially available resin Amberlyst A-31 was efficiently used to promote the propargylation of aldehydes using potassium allenyltrifluoroborate. The method is simple and fast, and the products were obtained in short reaction times in high yields and purity at room temperature in a regio- and chemoselective manner.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are additional experimental procedures and 1H, 13C, 19F, and 11B NMR for all synthesized compounds.
- Supporting Informtion
-
References
- 1 Yus M, Gonzalez-Gomez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
- 2 Ding C-H, Hou X-L. Chem. Rev. 2011; 111: 1914
- 3a Wisniewska HM, Jarvo ER. J. Org. Chem. 2013; 78: 11629
- 3b Bejjani J, Botuha C, Chemla F, Ferreira F, Magnus S, Perez-Luna A. Organometallics 2012; 31: 4876
- 4a Fandrick DR, Saha J, Fandrick KR, Sanyal S, Ogikubo J, Lee H, Roschangar F, Song JH. J, Senanayake CH. Org. Lett. 2011; 13: 5616
- 4b Chemla F, Ferreira F. Synlett 2006; 2613
- 4c Chemla F, Ferreira F, Hebbe V, Stercklen E. Eur. J. Org. Chem. 2002; 1385
- 4d Poisson J-F, Normant JF. J. Org. Chem. 2000; 65: 6553
- 4e Zweifel G, Hahn G. J. Org. Chem. 1984; 49: 4565
- 5a Millan A, de Cienfuegos LA, Martin-Lasanta A, Campana AG, Cuerva JM. Adv. Synth. Catal. 2011; 353: 73
- 5b Furata K, Ishiguro M, Haruta R, Ikeda N, Yamamoto H. Bull. Chem. Soc. Jpn. 1984; 57: 2768
- 5c Ishiguro M, Ikeda N, Yamamoto H. J. Org. Chem. 1982; 47: 2225
- 6a Guo LN, Gao HJ, Mayer P, Knochel P. Chem. Eur. J. 2010; 16: 9829
- 6b Pearson NR, Hahn G, Zweifel G. J. Org. Chem. 1982; 47: 3364
- 6c Guillerm-dron D, Capmau ML, Chodkiewicz W. Tetrahedron Lett. 1972; 37
- 7a Reich HJ, Holladay JE, Walker TG, Thompson JL. J. Am. Chem. Soc. 1999; 121: 9769
- 7b Bour C, Suffert J. Eur. J. Org. Chem. 2006; 1390
- 7c Corey EJ, Rucker C. Tetrahedron Lett. 1982; 23: 719
- 8a Lambert C, von Ragué Schleyer P. Angew. Chem., Int. Ed. Engl. 1994; 33: 1129
- 8b Saniere-Karila M, Capmau ML, Chodkiewicz W. Bull. Soc. Chim. Fr. 1973; 3371
- 9a Brawn RA, Panek JS. Org. Lett. 2007; 9: 2689
- 9b Sammtleben F, Noltemeyer M, Bruckner R. Tetrahedron Lett. 1997; 38: 3893
- 9c Danheiser RL, Carini DJ. J. Org. Chem. 1980; 45: 3925
- 10a Chatterjee PN, Roy S. J. Org. Chem. 2010; 75: 4413
- 10b Banerjee M, Roy S. Org. Lett. 2004; 6: 2137
- 10c McCluskey A, Muderawan M, Young DJ. Synlett 1998; 909
- 10d Mukaiyama T, Harada T. Chem. Lett. 1981; 621
- 10e Lequan M, Guillerm G. J. Organomet. Chem. 1973; 54: 153
- 11a Bhakta U, Sullivan E, Hall DG. Tetrahedron 2014; 70: 678
- 11b Nowrouzi F, Batey RA. Angew. Chem. Int. Ed. 2013; 52: 892
- 11c Xing C-H, Liao Y-X, Zhang Y, Sabarova D, Bassous M, Hu Q-S. Eur. J. Org. Chem. 2012; 1115
- 11d Hirayama LC, Haddad TD, Oliver AG, Singaram B. J. Org. Chem. 2012; 77: 4342
- 11e Jain P, Wang H, Houk KN, Antilla JC. Angew. Chem. Int. Ed. 2012; 51: 1391
- 11f Chen M, Roush WR. J. Am. Chem. Soc. 2012; 134: 10947
- 11g Reddy LR. Org. Lett. 2012; 14: 1142
- 11h Brown HC, Khire UR, Narla GJ. J. Org. Chem. 1995; 60: 8130
- 11i Farve E, Gaudemar M. J. Organomet. Chem. 1974; 76: 297
- 12 Tri-n-butyltin Compounds [MAK Value Documentation, 1990]. The MAK Collection for Occupational Health and Safety. Wiley-VCH; Weinheim: 2012: 316
- 13 Molander GA, Figueroa R. Aldrichimica Acta 2005; 38: 49
- 14 Science of Synthesis: Boron Compounds. Vol. 6. Kaufmann DE, Matteson DS. Thieme; Stuttgart: 2005
- 15a Bernardini R, Oliva A, Paganelli A, Menta E. Chem. Lett. 2009; 38: 750
- 15b Matteson DS. Tetrahedron 1998; 54: 10555
- 16 Oliveira RA, Silva RO, Molander GA, Menezes PH. Magn. Res. Chem. 2009; 47: 873
- 17 Petrillo DE, Kohli RK, Molander GA. J. Am. Soc. Mass Spectrom. 2007; 18: 404
-
18 Trost BM. Science 1991; 254: 1471
- 19 Oliveira RA, Savegnago L, Jesse CR, Menezes PH, Molander GA, Nogueira CW. Basic Clin. Pharmacol. Toxicol. 2009; 104: 448
- 20 Couto TR, Freitas JC. R, Cavalcanti IH, Oliveira RA, Menezes PH. Tetrahedron 2013; 69: 7006
- 21 Li QR, Gu CZ, Yin H. Chin. J. Chem. 2006; 24: 72
-
22 Chen J, Captain B, Takenaka N. Org. Lett. 2011; 13: 1654
- 23 Ma X, Wang JX, Li S, Wang KH, Huang D. Tetrahedron 2009; 65: 8683
- 24 Commercial product, available from Aurora Fine Chemicals, USA; CAS Number: 1342503-79-0.
- 25 Wu S, Huang B, Gao X. Synth. Commun. 1990; 20: 1279