Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate

Túlio R. Couto; Jucleiton J. R. Freitas; Juliano C. R. Freitas; Italo H. Cavalcanti; Paulo H. Menezes; Roberta A. Oliveira

doi:10.1055/s-0034-1379163

Synthesis, Table of Contents

Synthesis 2015; 47(01): 71-78
DOI: 10.1055/s-0034-1379163

paper

Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate

Túlio R. Couto

^aDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50740-540 Recife-PE, Brazil

,

Jucleiton J. R. Freitas

^aDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50740-540 Recife-PE, Brazil

,

Juliano C. R. Freitas

^bUnidade de Educação e Saúde, Universidade Federal de Campina Grande, 58175-000 Cuité-PB, Brazil Fax: +55(81)21268402 Email: roberta.ayres@pq.cnpq.br

,

Italo H. Cavalcanti

^aDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50740-540 Recife-PE, Brazil

,

Paulo H. Menezes

^aDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50740-540 Recife-PE, Brazil

,

Roberta A. Oliveira*

^aDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50740-540 Recife-PE, Brazil

› Author Affiliations

Abstract

All articles of this category

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.

Key words

propargylation - potassium organotrifluoroborates - Amberlyst A-31

Full Text

References

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

Supplementary Material

Supporting Informtion