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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

One-Pot, Regioselective Synthesis of Homopropargyl Alcohols using Propargyl Bromide and Carbonyl Compound by the Mg-mediated Reaction under Solvent-free Conditions

Author(s): Xiaofang Ma*, Shunxi Li, Samrat Devaramani *, Guohu Zhao and Daqian Xu

Volume 17, Issue 6, 2020

Page: [438 - 442] Pages: 5

DOI: 10.2174/1570178616666190926104037

Price: $65

Abstract

The elimination of volatile organic solvents in organic synthesis is the most important goal in “Green” chemistry. We report a simple, efficient and facile method for the addition of progargyl bromide to carbonyl compounds using Mg metal as a mediator under solvent-free conditions which could regioselectively generate homopropargyl alcohols efficiently in good to excellent yields. The procedure has advantages such as short reaction time, operationally simple, excellent product yields, high regioselectivity and organic solvent-free.

Keywords: Mg powder, propargylation, solvent-free, homopropargyl alcohol, homopropargyl alcohols, organic synthesis.

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[1]
Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., 2010, 107, 862.
[http://dx.doi.org/10.1002/ange.19951070710]
[2]
Zou, Y.; Gutierrez, O.; Sader, A.C.; Patel, N.D.; Fandrick, D.R.; Busacca, C.A.; Fandrick, K.R.; Kozlowski, M.; Senanayake, C.H. Org. Lett., 2017, 19(22), 6064-6067.
[http://dx.doi.org/10.1021/acs.orglett.7b02845] [PMID: 29095633]
[3]
Usanov, D.L.; Yamamoto, H. Angew. Chem. Int. Ed. Engl., 2010, 49(44), 8169-8172.
[http://dx.doi.org/10.1002/anie.201002751] [PMID: 20859976]
[4]
Denmark, S.E.; Wynn, T. J. Am. Chem. Soc., 2001, 123(25), 6199-6200.
[http://dx.doi.org/10.1021/ja016017e] [PMID: 11414863]
[5]
Brown, H.C.; Khire, U.R.; Narla, G.; Racherla, U.S. J. Org. Chem., 1995, 60, 544.
[http://dx.doi.org/10.1021/jo00108a014]
[6]
Iseki, K.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Asymmetry, 1998, 9, 2889.
[http://dx.doi.org/10.1016/S0957-4166(98)00290-0]
[7]
Zhang, Y.; Zhang, H.; Liu, L.Y.; Wang, X.; Chang, W.X.; Jing, L.I. Chem. J. Chin. Univ., 2012, 33, 2447.
[8]
Trost, B.M.; Ngai, M.Y.; Dong, G. Org. Lett., 2011, 13(8), 1900-1903.
[http://dx.doi.org/10.1021/ol200043n] [PMID: 21391717]
[9]
LI. Chin. J. Chem., 2006, 24, 72.
[10]
Lee, S.Y.; Chu, S.F.; Chang, Y.T.; Wang, S.H. Tetrahedron Lett., 2004, 45(7), 1551.
[http://dx.doi.org/10.1016/j.tetlet.2003.12.058]
[11]
Haddad, T.D.; Hirayama, L.C.; Buckley, J.J.; Singaram, B. J. Org. Chem., 2012, 77(2), 889-898.
[http://dx.doi.org/10.1021/jo201980b] [PMID: 22148263]
[12]
Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Yokoyama, M. J. Org. Chem., 1984, 49, 3904.
[http://dx.doi.org/10.1021/jo00195a006]
[13]
Hojo, M.; Sakuragi, R.; Okabe, S.; Hosomi, A. Chem. Commun. (Camb.), 2001, 4, 357.
[http://dx.doi.org/10.1039/b009351n]
[14]
Bandini, M.; Cozzi, P.G.; Melchiorre, P.; Tino, R.; Umani-Ronchi, A. Tetrahedron Asymmetry, 2001, 12, 1063.
[http://dx.doi.org/10.1016/S0957-4166(01)00182-3]
[15]
Wang, J.X.; Jia, X.; Meng, T.; Li, X. Synthesis, 2005, 17, 2838.
[http://dx.doi.org/10.1055/s-2005-872178]
[16]
Pogorelić, I.; Filipan, M.; Cepanec, I.; Litvić, M. J. Mol. Catal. Chem., 2007, 274, 202.
[http://dx.doi.org/10.1016/j.molcata.2007.05.020]
[17]
Bahadoor, A.B.; Micalizio, G.C. Org. Lett., 2006, 8(6), 1181-1184.
[http://dx.doi.org/10.1021/ol0600786] [PMID: 16524298]
[18]
Shi, S.L.; Xu, L.W.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc., 2010, 132, 6638.
[19]
Ma, X.; Wang, J.X.; Li, S.; Wang, K.H.; Huang, D. Tetrahedron, 2010, 65, 8683.
[http://dx.doi.org/10.1016/j.tet.2009.08.051]
[20]
Guo, L.N.; Gao, H.; Mayer, P.; Knochel, P. Chemistry, 2010, 16(32), 9829-9834.
[http://dx.doi.org/10.1002/chem.201000523] [PMID: 20572180]
[21]
Hirayama, L.C.; Haddad, T.D.; Oliver, A.G.; Singaram, B. J. Org. Chem., 2012, 77(9), 4342-4353.
[http://dx.doi.org/10.1021/jo300260a] [PMID: 22497595]
[22]
Reddy, L.R. Org. Lett., 2012, 14(4), 1142-1145.
[http://dx.doi.org/10.1021/ol300075n] [PMID: 22273041]
[23]
Anastas, P.; Eghbali, N. Chem. Soc. Rev., 2010, 39(1), 301-312.
[http://dx.doi.org/10.1039/B918763B] [PMID: 20023854]
[24]
Wei, Y.J.; Ren, H.; Wang, J.X. Tetrahedron Lett., 2008, 49, 5697.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.097]
[25]
Li, S.; Wang, J.X.; Wen, X.; Ma, X. Tetrahedron, 2011, 67, 849.
[http://dx.doi.org/10.1016/j.tet.2010.12.035]
[26]
Bai, L.; Wang, J.X. Adv. Synth. Catal., 2010, 350, 315.
[http://dx.doi.org/10.1002/adsc.200700361]

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