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Effect of Solvent and Acid-Base on Palladium (II)-catalyzed Dicarbonylation of Terminal Acetylenes: a General, Efficient and Stereoselective Synthesis of Maleic Diesters and Maleic Anhydrides

Jin-Hang Li

Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong 510650, China

Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, China

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Huan-Feng Jiang,

Huan-Feng Jiang

[email protected]

Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong 510650, China

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Ming-Cai Chen,

Ming-Cai Chen

Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong 510650, China

Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, China

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Jin-Hang Li,

Jin-Hang Li

Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong 510650, China

Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, China

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Huan-Feng Jiang,

Huan-Feng Jiang

[email protected]

Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong 510650, China

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Ming-Cai Chen,

Ming-Cai Chen

Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong 510650, China

Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, China

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First published: 26 August 2010

https://doi.org/10.1002/cjoc.20010190711

Citations: 6

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Abstract

The productions of maleic diesters and maleic anhydrides depend on the effect of solvent and acid-base in palladium-catalyzed dicarbonylation of terminal acetylenes. For primary and secondary alcohol in benzene, only maleic diesters were obtained stereospecifically from the dicarbonylation of acetylenes in the presence of PdCl₂, CuCl₂, and NaHCO₃. For tertiary alcohols, maleic anhydrides were synthesized selectively.

References

1(a) Chuisoli, G. P.; Venturello, C; Merzoni, S., Chem. Ind. (London) 1968, 977.
Google Scholar
(b) Tsuji, J; Nogi, T., J. Org. Chem. 1966, 31, 2641.
10.1021/jo01346a043
CAS Web of Science® Google Scholar
(c) Heck, R. F., J. Am. Chan. Soc. 1972, 94, 2712.
10.1021/ja00763a028
CAS Web of Science® Google Scholar
(d) Kasahara, A; Izumi, T; Suzuki, A., Bull. Chem. Soc. Jpn. 1977, 50, 1639.
10.1246/bcsj.50.1639
CAS Web of Science® Google Scholar
(e) Ji, J; Lu, X., Tetrahedron 1994, 30, 9067.
10.1016/S0040-4020(01)85373-4
Web of Science® Google Scholar
(f) Bruk, L. G.; Oshanina, I. V.; Kozlova, A. P.; Temkin, O. N.; Odintsov, K. Yu., Russ. Chem. Bull. 1998, 47, 1071.
10.1007/BF02503475
CAS Web of Science® Google Scholar
(g) Osakada, K; Doh, M. K.; Ozawa, F; Yamamoto, A., Organometallics 1990, 9, 2197.
10.1021/om00158a010
CAS Web of Science® Google Scholar
2(a) Alper, H; Despeyroux, B; Woell, J. B., Tetrahedron Lett. 1983, 24, 5691.
10.1016/S0040-4039(00)94174-1
CAS Web of Science® Google Scholar
(b) Zargarian, D; Alper, H., Organometallics 1991, 10, 2914.
10.1021/om00054a070
CAS Web of Science® Google Scholar
3(a) Cabriele, B; Costa, M; Salerno, G; Chiusoli, G. P., J. Chem. Soc., Perkin Trans. 1 1994, 83.
Google Scholar
(b) Gabriele, B; Costa, M; Salerno, G; Chiusoli, G. P., J. Chem. Soc., Perkin Trans. 1 1997, 147.
Google Scholar
4 Gabriele, B; Costa, M; Salerno, G; Chiusoli, G. P.; Costa, M., J. Organomet. Chem. 1995, 503, 21.
10.1016/0022-328X(95)05539-2
CAS Web of Science® Google Scholar
5(a) Gabriele, B; Salerno, G; Costa, M; Chiusoli, G. P., Chem. Commun. 1999, 1381.
Google Scholar
(b) Gabriele, B; Salerno, G; Costa, M; Chiusoli, G. P., Tetrahedron Lett. 1999, 40, 989.
10.1016/S0040-4039(98)02464-2
CAS Web of Science® Google Scholar
6 Sakurai, Y; Sakaguchi, S; Ishii, Y., Tetrahedron Lett. 1999, 40, 1701.
10.1016/S0040-4039(99)00031-3
CAS Web of Science® Google Scholar
7 Li, J; Jiang, H; Jia, L., Synth. Commum. 1999, 29, 3733.
10.1080/00397919908086012
CAS Web of Science® Google Scholar
8 For the effect of sovent and acid-base on palladium carbonylation of terminal acetylenes, see; Li, J.; Jiang, H.; Jia, L.; Feng, A., J. Org. Chem. 1999, 64, 5984.
10.1021/jo982345u
CAS Web of Science® Google Scholar
9(a) Itǒ, S; Fugise, Y; Sato, M., Tetrahedron Lett. 1969, 25, 691.
10.1016/S0040-4020(01)83279-8
Web of Science® Google Scholar
(b) Vaughan, W. R.; Andersen, K. S., J. Org. Chem. 1956, 21, 673.
10.1021/jo01112a023
CAS Web of Science® Google Scholar
10 Tsuji, J; Takahashi, M; Takahashi, T., Tetrahedron Lett. 1980, 21, 849.
10.1016/S0040-4039(00)71522-X
CAS Web of Science® Google Scholar

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Volume19, Issue7

July 2001

Pages 689-694

Effect of Solvent and Acid-Base on Palladium (II)-catalyzed Dicarbonylation of Terminal Acetylenes: a General, Efficient and Stereoselective Synthesis of Maleic Diesters and Maleic Anhydrides

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Effect of Solvent and Acid-Base on Palladium (II)-catalyzed Dicarbonylation of Terminal Acetylenes: a General, Efficient and Stereoselective Synthesis of Maleic Diesters and Maleic Anhydrides

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