A Convenient Synthesis of 2-Fluoro- and 2-Chloromalonic Esters Mediated by Hypervalent Iodine

Tsugio Kitamura; Kensuke Muta; Juzo Oyamada

doi:10.1055/s-0034-1378747

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(20): 3241-3245
DOI: 10.1055/s-0034-1378747

paper

A Convenient Synthesis of 2-Fluoro- and 2-Chloromalonic Esters Mediated by Hypervalent Iodine

Tsugio Kitamura*

Department of Chemistry of Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan eMail: kitamura@cc.saga-u.ac.jp

,

Kensuke Muta

Department of Chemistry of Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan eMail: kitamura@cc.saga-u.ac.jp

,

Juzo Oyamada

Department of Chemistry of Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan eMail: kitamura@cc.saga-u.ac.jp

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Abstract

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Abstract

Direct fluorination of malonic esters with a reagent system of iodosylbenzene and Et₃N·5HF gave the corresponding 2-fluoromalonic esters in good to high yields. Direct chlorination using iodosylbenzene and hydrochloric acid also provided the 2-chloromalonates in high yields.

Key words

2-fluoromalonic esters - 2-chloromalonic esters - hydrogen fluoride - hydrochloric acid - iodosylbenzene

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Referenzen

References
1 Harsanyi A, Sandford G. Org. Process Res. Dev. 2014; 18: 981

2a Chambers RD, Hutchinson J. J. Fluorine Chem. 1998; 92: 45
2b Chambers RD, Hutchinson J, Moilliet JS. PCT Int. Appl WO 9903802 A1 19990128, 1999
2c Chambers RD, Hutchinson J, Thomson J. PCT Int. Appl WO 9700848 A1 19970109, 1997

3 Umemoto T, Fukami S, Tomizawa G, Harasawa K, Kawada K, Tomita K. J. Am. Chem. Soc. 1990; 112: 8563
4 Patrick TB, Nadji S. J. Fluorine Chem. 1988; 39: 415
5 Purrington ST, Jones WA. J. Org. Chem. 1983; 48: 761
6 Chambers RD, Hutchinson J, Thomson J. J. Fluorine Chem. 1996; 78: 165

7a Umemoto T, Tomita K. Tetrahedron Lett. 1986; 27: 3271
7b Umemoto T, Tomita K, Kawada K. Org. Synth. 1990; 69: 129

8a Hoppe R, Dähne W, Mattauch H, Rödder K. Angew. Chem., Int. Ed. Engl. 1962; 1: 599
8b Weeks JL, Matheson M, Chernick C. J. Am. Chem. Soc. 1962; 84: 4612
8c Šmalc A, Lutar K, Kinkead SA. Inorg. Synth. 1992; 29: 1

9 Ishikawa N, Takaoka A. Chem. Lett. 1981; 107
10 Purrington ST, Woodard DL. J. Org. Chem. 1990; 55: 3423

11a Guenther A, Weintritt H, Boehm S. PCT Int. Appl WO 2005019154, 2005
11b Braun M, Brosch C. PCT Int. Appl WO 2002060838, 2002
11c Mueh T, Fiedler P, Weintritt H, Westerkamp W, Reinecke A. PCT Int. Appl WO 2002016304, 2002

12a Kitamura T, Kuriki S, Morshed MH, Hori Y. Org. Lett. 2011; 13: 2392
12b Kitamura T, Kuriki S, Muta K, Morshed MH, Muta K, Gondo K, Hori Y, Miyazaki M. Synthesis 2013; 45: 3125
12c Kitamura T, Muta K, Muta K. J. Org. Chem. 2014; 79: 5842
12d Hara S, Sekiguchi M, Ohmori A, Fukuhara T, Yoneda N. Chem. Commun. 1996; 1899
12e Yoshida M, Fujikawa K, Sato S, Hara S. ARKIVOC 2003; (vi): 36
12f Geary GC, Hope EG, Singh K, Stuart AM. Chem. Commun. 2013; 49: 9263
12g Suzuki S, Kamo T, Fukushi K, Hiramatsu T, Tokunaga E, Dohi T, Kita Y, Shibata N. Chem. Sci. 2014; 5: 2754

13 Carey FA, Sundberg RJ. Advanced Organic Chemistry . 4th ed. Kluwer Academic/Plenum Publishers; New York: 2000

14a Kitamura T, Tazawa Y, Morshed MH, Kobayashi S. Synthesis 2012; 44: 1159
14b Duan X, Zhou H, Tian X, Liu J, Ma J. Synthesis 2015; 47: 777

15 Lerman O, Rozen S. J. Org. Chem. 1983; 48: 724
16 Bergmann FD, Shahak I. Chem. Ind. (London) 1961; 591
17 Dubois J, Foures C, Bory S, Falcou S, Gaudry M, Marquet A. Tetrahedron 1991; 47: 1001
18 Zheng Z, Han B, Cheng P, Niu J, Wang A. Tetrahedron 2014; 70: 9814

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