Abstract
An easy, low cost, and green procedure is proposed for the 1, 4-addition of terminal alkynes to conjugated enones in water as a sole medium using easily accessible Zn[(l)Proline]2. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution and simple work up procedure.
Graphical Abstract
Recyclable Bis[(l)prolinato-N,O]Zn provides eminent, efficient, economical, environmentally benign protocol for the 1, 4-addition of terminal alkynes to conjugated enones in water as sole media. For the first time easily accessible, cheap catalyst was employed for such type of reaction.
Similar content being viewed by others
References
Lopez F, Minnaard AJ, Ferringa BL (2007) Acc Chem Res. doi: 10.1021/ar0501976
Alexakis A, Benhaim C (2002) Eur J Org Chem pp 3221–3236
House HO, Fischer WF Jr (1969) J Org Chem 34:3615
A review of this problem appears in the PhD thesis of J. H. Rea, University of Missouri, 1965; Dissertation Abstracts, 26 (1966) 5043
Hooz J, Layton RB (1971) J Am Chem Soc 93:7320
Pappo R, Collins PW (1972) Tetrahedron Lett 13:2627
Schwartz J, Carr DB, Hansen RT, Dayrit FM (1980) J Org Chem 45:3053
Sinclair JA, Molander GA, Brown HC (1977) J Am Chem Soc 99:954
Fujishima H, Takada E, Hara S, Suzuki A (1992) Chem Lett 695
Chong JM, Shen L, Taylor NJ (2000) J Am Chem Soc 122:1822
Bergdahl M, Eriksson M, Nilsson M, Olsson T (1993) J Org Chem 58:7238
Kim S, Lee JM (1990) Tetrahedron Lett 31:7627
Trost BM (2009) A H Weiss Adv Synth Catal 351:963
Yamashita M, Yamada K, Tomioka K (2005) Org Lett 7:2369
Chena L, Chao-Jun Li (2004) Chem Commun pp 2362–2364
Nishimura T, Washitake Y, Nishiguchi Y, i Maeda Y, Uemura S (2004) Chem Commun pp 1312–1313
Kovalev IP, Nikishin GI (1990) Tetrahedron Lett 31:7063
Picquet M, Bruneau C, Dixneuf PH (1999) Tetrahedron 55:3937
Chang S, Na Y, Choi E, Kim S (2001) Org Lett 3:2089
Lerum RV, Chisholm JD (2004) Tetrahedron Lett 45:6591
Knopfel TF, Carreira EM (2003) J Am Chem Soc 125:6054–6055
Cui S, Walker SD, Woo JCS, Borths CJ, Mukherjee H, Chen MJ, Faul MM (2010) J Am Chem Soc 132:436
Stork G, Borch R (1964) J Am Chem Soc 86:935
Johnson WS, Jensen NP, Hooz J (1968) E J Leopold 90:5872
Picquet M, Bruneau C, Dixneuf PH (1999) Tetrahedron 55:3937
Reisch J (1965) Arch Pharm 298:591
Pappo R, Collins PW (1972) Tetrahedron Lett 26:2627–2630
Bruhn M, Brown CH, Collins PW, Palmer JR, Dayanl EZ, Pappo R (1976) Tetrahedron Lett 4:230–235
Stork G, McMurry JE, Borch R (1964) J Am Chem Soc 86:936
Glass TE (1971) Tetrahedron Lett p 2578
Kobayashi S, Nagayama S, Busujima T (1998) J Am Chem Soc 120:8287–8288
Darbre T, Machuquerio M (2003) Chem Commun pp 1090–1091
Lopez RF, Kofoed J, Machuqueiro M, Darbre T (2005) Eur J Org Chem pp 5268–5279
Sivamurugan V, Vinu A, Palanichamy M, Murugesan V (2006) Hetroatom Chem 17:267–271
Kidwai M, Poddar R, Diwaniyan S, Kuhad RC (2009) Adv Synth Catal 351:589–595
Kidwai M, Bhardwaj S, Mishra NK, Bansal V, Kumar A, Mozumdar S (2009) Catal Commun 10:1514–1517
Kidwai M, Bhatnagar D, Mishra NK, Bansal V (2008) Catal Commun 9:2525–2547
Haldar MK, Scott MD, Sule N, Srivastava DK, Mallik S (2008) Bioorg Med Chem Lett 18:2373–2376
Deb ML, Bhuyan PJ (2005) Tetrahedron Lett 46:6453–6456
Yamashita M, Yamada K, Tomioka K (2005) Org Lett 7:2369–2371
Lonibala R, Rao T (1991) Crys ResTechnol 26:77–80
Acknowledgments
The authors (A. Jain and S. Bhardwaj) are thankful to UGC and CSIR, New Delhi for their junior research fellowship.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Kidwai, M., Jain, A. & Bhardwaj, S. 1, 4-Addition of Terminal Alkynes to Conjugated Enones in Water Using Green Catalyst Bis[(l)prolinato-N,O]Zn—An Environmentally Benign Protocol. Catal Lett 141, 183–190 (2011). https://doi.org/10.1007/s10562-010-0451-8
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-010-0451-8