Synlett, Table of Contents Synlett 2012; 23(8): 1221-1224DOI: 10.1055/s-0031-1290885 letter © Georg Thieme Verlag Stuttgart · New YorkEfficient Pyrimidone-Promoted Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling Reaction Hong-Ping Zhang* Department of Biology and Chemistry Engineering, Shaoyang University, Shaoyang 422000, P. R. of China, Fax: +86(739)5363951 Email: zhp4901@sina.com , You-Zhi Dai Department of Biology and Chemistry Engineering, Shaoyang University, Shaoyang 422000, P. R. of China, Fax: +86(739)5363951 Email: zhp4901@sina.com , Xi Zhou Department of Biology and Chemistry Engineering, Shaoyang University, Shaoyang 422000, P. R. of China, Fax: +86(739)5363951 Email: zhp4901@sina.com , Huang Yu Department of Biology and Chemistry Engineering, Shaoyang University, Shaoyang 422000, P. R. of China, Fax: +86(739)5363951 Email: zhp4901@sina.com› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract An efficient Pd(OAc)2/orotic acid catalytic system has been developed for Suzuki–Miyaura cross-coupling reaction of halides with aryl- and vinylboronic acids. The use of pyrimidone as ligand makes this method useful and attractive for the synthesis of stilbenes and derivative compounds. An attractive feature of this method is the tolerance of functional groups in both substrates. Keywords KeywordsSuzuki–Miyaura cross-coupling reaction - pyrimidones - vinylboronic acids - halides - stilbenes Full Text References References and Notes 1a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457 1b Stanforth SP. Tetrahedron 1998; 54: 263 1c Kirshhoff JH, Dai C, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 1945 1d Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685 1e Godoy F, Segarra C, Poyatos M, Peris E. Organometallics 2011; 30: 684 1f Kotha S, Chavan AS, Shaikh M. J. Org. Chem. 2012; 77: 482 2a Littke AF, Dai C, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020 2b Altenhoff G, Goddard R, Lehmann CW, Glorius F. J. Am. Chem. Soc. 2004; 126: 15195 2c Diebolt O, Costa RC, Braunstein P, Cavallo L, Nolan SP, Slawin AM. Z, Cazin CS. J. Organometallics 2010; 29: 1443 2d Marion N, Nolan SP. Acc. Chem. Res. 2008; 41: 1440 3a Jo TS, Kim SH, Shin J, Bae C. J. Am. Chem. Soc. 2009; 131: 1656 3b Magnus P, Sane N, Fauber BP. J. Am. Chem. Soc. 2009; 131: 16045 3c Baratta W, Benedetti F, Fanfoni L, Felluga F, Magnolia S, Putignano E, Rigo P. Organometallics 2010; 29: 3563 4 Bedford RB, Cazin CS. J. Chem. Commun. 2001; 17: 1540 5 Botella L, Najera C. Angew. Chem. Int. Ed. 2002; 41: 179 6a Grasa GA, Hillier AC, Nolan SP. Org. Lett. 2001; 3: 1077 6b Eisenstecken BE, Kopacka D, Wurst K, Moller T, Pevny F, Winter RF, Bildstein B. Organometallics 2010; 29: 3169 7a Schneider SK, Herrmann WA, Herdtweck E. J. Mol. Catal. A: Chem. 2006; 245: 248 7b Liao C.-Y, Chan K.-T, Zeng J.-Y, Hu C.-H, Tu C.-Y, Lee HM. Organometallics 2007; 26: 692 7c Li J.-H, Hu X.-C, Xie Y.-X. Tetrahedron Lett. 2006; 47: 9239 8a Cano R, Ramon DJ, Yus M. Tetrahedron 2011; 67: 5432 8b Li C, Li X.-Q, Zhang C. J. Chem. Res., Synop. 2008; 9: 525 8c Du Z, Zhou W, Wang F, Wang J.-X. Tetrahedron 2011; 67: 4914 8d Zarei A, Khazdooz L, Hajipour AR, Rafiee F, Azizi G, Abrishami F. Tetrahedron Lett. 2012; 53: 406 9 Aizawa S, Majumder A, Yokoyama Y, Tamai M, Maeda D, Kitamura A. Organometallics 2009; 28: 6067 10 Yesilel OZ, Ölmez H. J. Therm. Anal. Calorim. 2007; 89: 555 11 Typical Experimental Procedure for the Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling Reaction:A mixture of aryl halide 1 (0.5 mmol), arylboronic acid 2 (0.6 mmol), PdCl2 (0.0075 mmol), orotic acid (0.015 mmol), and acetone (5 mL) was stirred in a Schlenk tube at 80 °C under Ar for 10 h. Complete consumption of the starting material was monitored by TLC and GC–MS analysis. After the reaction was complete, the mixture was poured into EtOAc, washed with brine (3 × 10 mL), and extracted with EtOAc. The combined organic layers were dried over anhyd Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane or hexane–EtOAc) providing the desired coupled product 3 in 96% yield.4-Methoxybiphenyl (3):12 white solid; mp 86.5–87.2 °C (lit. mp 86 °C). 1H NMR (400 MHz, CDCl3): δ = 7.54 (t, J = 9.4 Hz, 4 H), 7.41 (t, J = 9.4 Hz, 2 H), 7.31 (t, J = 9.6 Hz, 1 H), 6.98 (d, J = 8.9 Hz, 2 H), 3.85 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 159.1, 140.7, 133.7, 128.7, 128.1, 126.7, 126.6, 114.2, 55.3. LRMS (EI, 70 eV): m/z (%) = 186 (16) [M+ + 2], 184 (100) [M+], 153 (45), 119 (25) 12a Beadle JB, Korzeniowski SH, Rosenberg DE, Garcia-Slanga BJ, Gokel GW. J. Org. Chem. 1984; 49: 1594 12b Li J.-H, Liu W.-J. Org. Lett. 2004; 6: 2809 12c Tang Z.-Y, Hu Q.-S. J. Am. Chem. Soc. 2004; 126: 3058 Supplementary Material Supplementary Material Supporting Information
