Dichlorination of β-Keto Esters and 1,3-Diketones Mediated by Oxone/Aluminum Trichloride Mixture in Aqueous Medium

Vasileios Giannopoulos; Nikolaos Katsoulakis; Ioulia Smonou

doi:10.1055/s-0041-1737412

Synthesis, Table of Contents

Synthesis 2022; 54(10): 2457-2463
DOI: 10.1055/s-0041-1737412

paper

Dichlorination of β-Keto Esters and 1,3-Diketones Mediated by Oxone/Aluminum Trichloride Mixture in Aqueous Medium

Vasileios Giannopoulos

,

Nikolaos Katsoulakis

,

Ioulia Smonou ∗

Abstract

All articles of this category

This work is dedicated to Professor G. J. Karabatsos on the occasion of his 90^th birthday

Abstract

A new method for the α,α-dichlorination of β-keto esters using Oxone/aluminum trichloride mixture in aqueous medium has been developed. This useful process has also been applied successfully for the dichlorination of 1,3-diketones. The dichlorinated compounds have been produced in one step, high yields, and short reaction times.

Key words

Oxone - aluminum trichloride - dichlorination - β-dicarbonyl

Full Text

References

References
1 Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
2 Wilcken R, Zimmermann MO, Lange A, Joerger AC, Boeckler FM. J. Med. Chem. 2013; 56: 1363
3 Fang WY, Ravindar L, Rakesh KP, Manukumar HM, Shantharam CS, Alharbi NS, Qin HL. Eur. J. Med. Chem. 2019; 173: 117
4 Uoto K, Ohsuki S, Takenoshita H, Ishiyama T, Iimura S, Hirota Y, Mitsui I, Terasawa H, Soga T. Chem. Pharm. Bull. 1997; 45: 1793
5 Nakayama K, Kawato HC, Inagaki H, Nakajima R, Kitamura A, Someya K, Ohta T. Org. Lett. 2000; 2: 977
6 Sadhukhan S, Santhi J, Baire B. Chem. Eur. J. 2020; 26: 7145
7 Nicolaou KC, Lim YH, Becker J. Angew. Chem. Int. Ed. 2009; 48: 3444
8 Chung W, Vanderwal CD. Angew. Chem. Int. Ed. 2016; 55: 4396
9 Song X, Tian S, Zhao Z, Zhu D, Wang M. Org. Lett. 2016; 18: 3414
10 Huang F, Xie J, Sun J, Wang Y, Dong X, Qi L, Zhang B. Org. Lett. 2016; 18: 684
11 Bergeron-Brlek M, Teoh T, Britton R. Org. Lett. 2013; 15: 3554
12 Yin Q, You S.-L. Org. Lett. 2014; 16: 1810
13 Yamamoto T, Ishibuchi S, Ishizuka T, Haratake M, Kunieda T. J. Org. Chem. 1993; 58: 1997
14 Pinho P, Kalayanov G, Westerlind H, Rosenquist Å, Wähling H, Sund C, Almeida M, Ayesa S, Tejbrant J, Targett-Adams P, Eneroth A, Lindqvist A. Bioorg. Med. Chem. Lett. 2017; 27: 3468
15 Mendonça GF, Sindra HC, de Almeida LS, Esteves PM, de Mattos MC. S. Tetrahedron Lett. 2009; 50: 473
16 Liu W, Tan L, Zhou P, Chen C, Zhang Q. Synthesis 2013; 45: 2600
17 Kim J.-J, Kweon D.-H, Cho S.-D, Kim H.-K, Lee S.-G, Yoon Y.-J. Synlett 2006; 194
18 Duan X, Zhou H, Tian X, Liu J, Ma J. Synthesis 2015; 47: 777
19 Pu X, Li Q, Lu Z, Yang X. Eur. J. Org. Chem. 2016; 5937
20 Zhang Y, Shibatomi K, Yamamoto H. J. Am. Chem. Soc. 2004; 126: 15038
21 Hussain H, Green IR, Ahmed I. Chem. Rev. 2013; 113: 3329
22 Montgomery RE. J. Am. Chem. Soc. 1974; 96: 7820
23 Zolfigol MA, Bagherzadeh M, Mallakpour S, Chehardoli G, Kolvari E, Choghamarani AG, Koukabi N. Catal. Commun. 2007; 8: 256
24 Wu S, Ma H, Lei Z. Tetrahedron 2010; 66: 8641
25 Swamy P, Kumar MA, Reddy MM, Narender N. Chem. Lett. 2012; 41: 432
26 Zhou ZS, Li L, He XH. Chin. Chem. Lett. 2012; 23: 1213
27 Zibuck R, Streiber JM. J. Org. Chem. 1989; 54: 4717
28 Presset M, Michelet B, Guillot R, Bour C, Bezzenine-Lafollée S, Gandon V. Chem. Commun. 2015; 51: 5318
29 Zheng Z, Han B, Cheng P, Niu J, Wang A. Tetrahedron 2014; 70: 9814
30 Zheng LS, Phansavath P, Ratovelomanana-Vidal V. Org. Lett. 2018; 20: 5107
31 Coffey KE, Murphy GK. Synlett 2015; 26: 1003

Supplementary Material

Supporting Information