Application of Suzuki cross-coupling reaction catalyzed by ligandless palladium chloride in the synthesis of liquid crystals

Synthetic Communications

Volumn 37, Issue 13, 2007, Pages 2203-2208

  Huang, Mei ^a   Cheng, Jianhua ^a   Tao, Xiaochun ^a   Wei, Mingwang ^a   Shen, Dong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Ligandless palladium catalysis; Suzuki cross coupling; trans cyclohexyl biphenyl liquid crystals

Indexed keywords

ARTICLE; CATALYST; CROSS COUPLING REACTION; CRYSTALLIZATION; LIQUID CRYSTAL; ROOM TEMPERATURE; SPECTROSCOPY; SUZUKI REACTION;

EID: 34447131572     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701397292     Document Type: Article

References (16)

1. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. The palladium-catalyzed cross-coupling reaction of phenylboronoc acid with haloarenes in the presence of bases. Synth. Commun. 1981, 11 (7), 513-519;
2. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1997; p. 73.
3. 2I (L = triarylphosphine) complexes. J. Am. Chem. Soc. 1997, 119, 12441-12453;
4. (b) O'Keefe, D. F.; Dannok, M. C.; Marcuccio, S. M. Palladium catalyzed coupling of halobenzenes with arylboronic acids: Role of the triphenylphosphine. Tetrahedron Lett. 1992, 33, 6679-6680;
5. (c) Moreno-Manas, M.; Perez, M.; Pleixats, R. Palladium-catalyzed Suzuki-type self-coupling of arylboronic acids: A mechanistic study. J. Org. Chem. 1996, 61, 2346-2351.
6. Yasuyuki, G.; Makoto, T.; Maki, N. Preparation of biaryls by coupling reaction of aromatic boronic acids with aryl compounds, JP9278676, Chem. Abstr. 1997, 127 (25), 553.
7. Yasuyuki, G.; Masaki, N.; Katsuhiko, K. Method for preparation of biaryl derivatives by coupling reaction on arylboronic acids, JP2000336045, Chem. Abstr. 2001, 134 (3), 527.
8. Guo, M. P.; Zhou, L.; He, R. Study on Suzuki reaction for the synthesis of fluorinated liquid crystals catalyzed by P, N coordinated palladium complexes. J. Mol. Cat. (China) 2006, 20 (3), 203-206.
9. Bellina, F.; Carpita, A.; Rossi, R. Palladium catalysts for the Suzuki cross-coupling reactions: An overview of recent advances. Synthesis 2004, 15, 2419-2440.
10. Tao, X. C.; Zhao, Y. Y.; Shen, D. A simple and highly efficient catalytic system for Suzuki cross-coupling using ligandless palladium chloride. Synlett 2004, 2, 359-361.
11. (a) Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457;
12. (b) Moreno-Manax, M.; Perez, M.; Pleixats, R. Palladium-catalyzed Suzuki-type self-coupling of arylboronic acids: A mechanistic study. J. Org. Chem. 1996, 61, 2346.
13. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004; p. 50.
14. Li, J.; An, Z. W.; Yang, Y. Progress of liquid crystal materials for TFT LCD. Chin. J. Liq. Cryst. Displays 2002, 17 (2), 104.
15. Cheng, N. L. Solvents Handbook, 3rd Edn.; Chemical Industry Press: Beijing, 2002; p. 789.
16. Eike, P.; Volker, M. Process and catalysts for the preparation of bisaryl compounds by the coupling of arylmagnesium chlorides with aryl chlorides in the presence of phosphine ligands[P], Ger. Offen. DE 4326169 A1, Feb. 9, 1995.