Pd-catalyzed one-pot multicomponent coupling reaction for the highly regioselective synthesis of polysubstituted benzenes

Organic Letters

Volumn 7, Issue 2, 2005, Pages 347-349

  Xi, Chanjuan ^a   Chen, Chao ^a   Lin, Jie ^a   Hong, Xiaoyin ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKYNE; BENZENE DERIVATIVE;

ARTICLE; CATALYST; SYNTHESIS;

EID: 13444292181     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047553p     Document Type: Article

References (44)

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36. Usually, the Sonogashira coupling is carried out in the presence of catalytic amounts of a palladium(II) complex as well as copper(I) iodide in an amine as a solvent. For reviews, see: (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549. (c) Rossi, R.; Carpita, A.; Bellina, F. Org. Prepr. Proced. Int. 1995, 27, 129-160. (d) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; pp 168-171. (e) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 203-229.
37. Usually, the Sonogashira coupling is carried out in the presence of catalytic amounts of a palladium(II) complex as well as copper(I) iodide in an amine as a solvent. For reviews, see: (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549. (c) Rossi, R.; Carpita, A.; Bellina, F. Org. Prepr. Proced. Int. 1995, 27, 129-160. (d) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; pp 168-171. (e) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 203-229.
38. Usually, the Sonogashira coupling is carried out in the presence of catalytic amounts of a palladium(II) complex as well as copper(I) iodide in an amine as a solvent. For reviews, see: (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549. (c) Rossi, R.; Carpita, A.; Bellina, F. Org. Prepr. Proced. Int. 1995, 27, 129-160. (d) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; pp 168-171. (e) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 203-229.
39. Usually, the Sonogashira coupling is carried out in the presence of catalytic amounts of a palladium(II) complex as well as copper(I) iodide in an amine as a solvent. For reviews, see: (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549. (c) Rossi, R.; Carpita, A.; Bellina, F. Org. Prepr. Proced. Int. 1995, 27, 129-160. (d) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; pp 168-171. (e) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 203-229.
40. Usually, the Sonogashira coupling is carried out in the presence of catalytic amounts of a palladium(II) complex as well as copper(I) iodide in an amine as a solvent. For reviews, see: (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549. (c) Rossi, R.; Carpita, A.; Bellina, F. Org. Prepr. Proced. Int. 1995, 27, 129-160. (d) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; pp 168-171. (e) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 203-229.
41. Kawasaki, T.; Yamamoto, Y. J. Org. Chem. 2002, 67, 5138-5141.
42. 4, and 280 μL (2.0 mmol) of triethylamine in 5 mL of THF was added 240 μL (2.2 mmol) of ethynylbenzene 1a. The reaction mixture was stirred for 12 h at 50°C, quenched with 2 N HCl, and extracted with ether. Purification of crude product was carried out by column chromatography on silica gel (dichloromethane/ petroleum ether = 1/2).
43. 2 = 0.0893, GOF = 1.034.
44. Ethyl 2-bromoacrylate was prepared according to the literature. Dachon, J. Goedken, V.; Walborsky, H. M. J. Org. Chem. 1989, 54, 1006-1012.