Synthesis of 4-halo-2 (5H)-furanones and their suzuki-coupling reactions with organoboronic acids. A general route to 4-aryl-2 (5 H) -furanones

Sheng-Ming Ma

[email protected]

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Zhang-Jie Shi,

Zhang-Jie Shi

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Sheng-Ming Ma,

Sheng-Ming Ma

[email protected]

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

Zhang-Jie Shi,

Zhang-Jie Shi

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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First published: 26 August 2010

https://doi.org/10.1002/cjoc.20010191220

Citations: 9

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Abstract

4-Halo-2(5H)-furanones were prepared by the halolactonization of 2,3-allenoic acids. The subsequent Suzuki coupling reaction of 4-halo 2(5H)-furanones with aryl boronic acids was carried out to produce 4-aryl-2(5H)-furanones in excellent yields.

References

1(a) Brima, T. S., US 4968817, 1990.
Google Scholar
[Chem. Abstr. 1991, 114, 185246y].
Google Scholar
(b) Tanabe, A., Kokai. Tokyo. Koho JP. 63211276,.
Google Scholar
[88211276], 1988.
Google Scholar
[Chem. Abstr. 1989, 110, 94978q].
Google Scholar
(c) Lee, G. C. M., Eur. Pat. EP. 372940, 1990.
Google Scholar
[Chem. Abstr. 1990, 113, 191137j].
Google Scholar
(d) Ducharme, Y; Gauthier, J. Y; Prasit, P; Leblanc, Y; Wang, Z; Leger, S; Thrien, M., PCT Int. Appl. WO 9500501, 1995.
Google Scholar
[Chem. Abstr. 1996, 124, 55954y].
Google Scholar
(e) Lee Gary, C. M; Gast, M. E., PCT Int. Appl. WO. 9116055, 1991.
Google Scholar
[Chem. Abstr. 1992, 116, 59197m].
Google Scholar
2(a) Ma, S; Shi, Z., J. Org. Chem. 1998, 63, 6387, for a summary of known procedures, see references cited therein.
10.1021/jo9804588
CAS PubMed Web of Science® Google Scholar
(b) Ma, S., Duan, D; Shi, Z., Org. Lett. 2000, 2, 1419.
10.1021/ol0057481
CAS PubMed Web of Science® Google Scholar
(c) Ma, S., Shi, Z; Wu, S., Tetrahedron; Asymmetry 2001, 12, 193.
10.1016/S0957-4166(01)00046-5
CAS Web of Science® Google Scholar
3 Ma, S; Yu, Z; Wu, S., Tetrahedron 2001, 57, 1585.
10.1016/S0040-4020(00)01149-2
CAS Web of Science® Google Scholar
4 Ma, S; Wu, S., Chem. Commun. 2001, 441.
Web of Science® Google Scholar
5 Ma, S; Wu, S., Tetrahedron Lett. 2001, 42, 4075.
10.1016/S0040-4039(01)00634-7
CAS Web of Science® Google Scholar
6 Ma, S; Shi, Z; Yu, Z., Tetrahedron Lett. 1999, 40, 2393.
10.1016/S0040-4039(99)00275-0
CAS Web of Science® Google Scholar
7 Ma, S; Shi, Z; Yu, Z., Tetrahedron 1999, 40, 12137.
10.1016/S0040-4020(99)00726-7
Web of Science® Google Scholar
8(a) Suzuki, A., Pure Appl. Chem. 1985, 57, 1749.
10.1351/pac198557121749
CAS Web of Science® Google Scholar
(b) Suzuki, A., Pure Appl. Chem. 1991, 63, 419.
10.1351/pac199163030419
CAS Web of Science® Google Scholar
(c) Suzuki, A., Pure Appl. Chem. 1994, 66, 213.
10.1351/pac199466020213
CAS Web of Science® Google Scholar
9 Venkruijsse, H. D; Brandsma, L., Synthesis of Acetylenes, Allenes and Cumulenes. A Laboratory Munual, Elsevier, Amsterman, The Netherlands, 1981, p. 33.
Google Scholar
10 Kresze, G; Runge, W; Ruch, E., Liebigs Ann. Chem. 1972 756, 112.
10.1002/jlac.19727560111
CAS Web of Science® Google Scholar
11 Mattesson, P. S., Tetrahedron 1989, 45, 1859.
10.1016/S0040-4020(01)80052-1
Web of Science® Google Scholar
12 Bamberger, E; Pamsel, W., J. Chem. Soc. 1903, 183, 289.
Google Scholar

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Volume19, Issue12

December 2001

Pages 1280-1284

Synthesis of 4-halo-2 (5H)-furanones and their suzuki-coupling reactions with organoboronic acids. A general route to 4-aryl-2 (5 H) -furanones

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Synthesis of 4-halo-2 (5H)-furanones and their suzuki-coupling reactions with organoboronic acids. A general route to 4-aryl-2 (5 H) -furanones

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