30 (s, 3H) 13 C NMR (100 MHz, CDCl 3 ): ? 140, Hz, 1H), 7.31 (t, J = 7.3 Hz, 1H) ,
39 (s, 3H) 13 C NMR (100 MHz, CDCl 3 ): ? 150(3-Methylbenzo[b]thiophen-2-yl)-isoquinoline (29) From 4-bromoisoquinoline (0.208 g, 1 mmol) and 3-methyl- g) yield as a yellow oil, pp.8-5380 ,
274 g, 1.5 mmol), 32 was obtained in 85% (0.249 g) yield as a white solid (mp 137-138 °C) 1 H NMR (400 MHz CDCl 3 ): ? 730 (s, 3H) 13 C NMR (100 MHz, CDCl 3 ): ? 142(4-tert-Butylphenyl)-3-methyl-benzo[b]thiophene (33) From 1-tert-butylbromobenzene (0.213 g, 1 mmol) and 5-chloro- 3-methylbenzothiophene (0.274 g, 1.5 mmol), 33 was obtained in 58% (0.182 g) yield as a white solid (mp 134-136 °C). 1 H NMR (400 MHz, CDCl 3 ): ? 7, (d, J = 8.3 Hz, 1H) 4H), 7.22 (d, J = 8.3 Hz, 1H), 2.36 (s, 3H), 1.30 (s, 9H). 13 C NMR (100 MHz ,
13 C NMR (100 MHz CDCl 3 ): ? 141, p.25 ,
(dd, J = 8.5, 1.8 Hz, 1H), 2.30 (s, 3H) 13 C NMR (100 MHz, CDCl 3 ): ? 150, 1920. ,
13 C NMR (100 MHz CDCl 3 ): ? 138 ,
CDCl 3 ): ? 140 Supporting information Copies of 1 H and 13 C NMR spectra of new compounds. References 1, (d, J = 8.5 Hz, 2H), 7.12 (d, J = 8.5 Hz, 2H). 13 C NMR (100 MHz, pp.1951-1958, 1990. ,
Palladium-Catalyzed Indole, Pyrrole, and Furan Arylation by Aryl Chlorides, The Journal of Organic Chemistry, vol.76, issue.2, pp.471-483, 2011. ,
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URL : http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3021639
For selected recent contributions on direct arylations of heteroaromatics from our laboratory: (a) Derridj, Chem. Eur. J. J, vol.13, issue.4, pp.1816-1819, 2011. ,
For selected examples of palladium-catalyzed direct arylation of thiophenes: (a), J. Am. Chem. Soc, vol.354, issue.124, pp.747-750, 2002. ,
Handbook of Organopalladium Chemistry for Organic Synthesis, Palladium in Heterocyclic Chemistry, pp.1851-1854, 2000. ,
Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the Use of Copper Iodide in the Reaction, Bulletin of the Chemical Society of Japan, vol.71, issue.2, pp.467-473, 1998. ,
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Heck-like coupling and Pictet???Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines, Tetrahedron, vol.63, issue.36, pp.8999-9006, 2007. ,
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For examples of intermolecular direct arylation of benzothiophenes using 5 mol-% Pd(OAc) 2 associated to a stoechiometric amount of quaternary ammonium salts or crown ethers as stabilizing agents: (a) Fournier Dit Chabert, J.; Joucla, L Tetrahedron J J, vol.40, issue.60, pp.1015-1017, 2004. ,
For recent examples of 2-arylbenzothiophenes synthesis: Duan, J. Org. Chem. Adv. Synth. Catal. Tetrahedron Adv. Synth. Catal. J. Org. Chem. Z.; Ranjit, S Org. Lett, vol.70, issue.12, pp.7578-7584, 1977. ,