Synthesis of mono-, di-, and tri- phenyl arenes by sequential photostimulated S(RN)1 and Pd(0)-catalyzed cross coupling reactions on aryl halides

Synlett

Volumn , Issue 2, 2000, Pages 230-232

  Córsico, Eduardo F ^a   Rossi, Roberto A ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

Cross coupling; Photostimulation; S(RN)1 reactions; Stille

Indexed keywords

BENZENE DERIVATIVE; HALIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; PHOTOSTIMULATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0041863520     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6503     Document Type: Article

References (22)

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3. For reviews see Mitchell, T. N. Synthesis 1992, 803; Farina, V.; Krishnamurthy, V.; Scott, W. J. In The Stille Reaction, Organic Reactions Vol. 50, Paquette, L. A., Ed.; Wiley: Chichester, 1997; p.1.
4. For reviews see Mitchell, T. N. Synthesis 1992, 803; Farina, V.; Krishnamurthy, V.; Scott, W. J. In The Stille Reaction, Organic Reactions Vol. 50, Paquette, L. A., Ed.; Wiley: Chichester, 1997; p.1.
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13. Gronowitz, S.; Peters, D. Heterocycles 1990, 30, 645. Otsubo, T.; Kono, Y.; Hozo, N.; Miyamoto, H. Aso, Y.; Ogura, F.; Tanaka, T.; Sawada, M. Bull. Chem. Soc. Jpn. 1993, 66, 2033. Lamba, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11723.
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15. RN1 Mechanism; ACS Monograph 178: Washington, DC, 1983.
16. (b) Morris, R. K. Comprehensive Organic Synthesis, Ed. Trost B. M. 1991, 4, 451.
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19. Córsico, E. F.; Rossi, R. A., Synlett 2000, 227.
20. - ion in liquid ammonia in 85% yield, see ref. 12.
21. 2 (0.056 g, 0.080 mmol, 5%) and the solution was heated to 80 °C during 3 h. The solution was filtered and water (50 mL) was added and then extracted three times with diethyl ether. The product was quantified by GLC using the internal standard method compared with authentic samples. Products were isolated by column chromatography and their spectroscopic data agreed with those reported in the literature, see Properties of Organic Compounds, Version 5.0, CRC Press Data Base, CRC Press: Boca Raton, 1996.
22. 4Sn. It is more difficult to transfer a methyl group than a phenyl ring, see ref. 2. No toluene was found in all these reactions.