Regioselective Synthesis of Trialkylpyrazines via Nickel-Catalyzed Negishi Cross-Coupling of Pyrazine Triflate

Abstract

A regioselective synthesis of trialkylpyrazines via nickel-catalyzed cross-coupling reaction of pyrazine triflate is reported. The 5-substituted 2,3-dimethylpyrazine derivatives including trail pheromone components of the ant Eutetramorium mocquerysi have been successfully synthesized in good yields by nickel-catalyzed Negishi cross-coupling reactions of pyrazine triflate mediated by alkyl and arylzinc halides.

Key words

trialkylpyrazine - pheromone - Negishi cross-coupling - pyrazine triflate - organozinc halide

• References

• 1a Müller R, Rappert S. Appl. Microbiol. Biotechnol. 2010; 85: 1315
• 1b Rajini KS, Aparna P, Sasikala Ch, Ramana ChV. Crit. Rev. Microbiol. 2011; 37: 99
• 2a Czerny M, Wagner R, Grosch W. J. Agric. Food Chem. 1996; 44: 3268
• 2b Lasekan O, Abbas KA. Trends Food Sci. Technol. 2010; 21: 494
• 2c Burdock GA, Carabin IG. Reg. Tox. Pharm. 2008; 50: 303
• 3a Tentschert J, Bestmann H.-J, Hölldobler B, Heinze J. Naturwissenschaften 2000; 87: 377
• 3b Hölldobler B, Morgan ED, Oldham NJ, Liebig J. J. Insect Physiol. 2001; 47: 369
• 3c Jones TH, Garraffo HM, Blum MS, Everett DM, Hastings H, Ware AB. J. Chem. Ecol. 1998; 24: 125
• 4a Dickschat JS, Wagner-Döbler I, Schulz S. J. Chem. Ecol. 2005; 31: 925
• 4b Dickschat JS, Wickel S, Bolten CJ, Nawrath T, Schulz S, Wittmann C. Eur. J. Org. Chem. 2010; 2687
• 5 Kai M, Haustein M, Molina F, Petri A, Scholz B, Piechulla B. Appl. Microbiol. Biotechnol. 2009; 81: 1001
• 6a Rizzi GP. J. Org. Chem. 1968; 33: 1333
• 6b Schulz S, Fuhlendorff J, Reichenbach H. Tetrahedron 2004; 60: 3863
• 7a Büchi G, Galindo J. J. Org. Chem. 1991; 56: 2605
• 7b Kurniadi TH, Rhlid RB, Juillerat M.-A, Gefflaut T, Bolte J, Berger RG. Tetrahedron 2003; 59: 6109
• 7c Guram AS, Jordan RF. J. Org. Chem. 1992; 57: 5994
• 7d Elmaaty TA, Castle LW. Org. Lett. 2005; 7: 5529
• 8a Ohta A, Ohta M, Igarashi Y, Saeki K, Yuasa K, Mori T. Heterocycles 1987; 26: 2449
• 8b Seeman JI, Paine JB III, Seccor HV, Im H.-S, Bernstein ER. J. Am. Chem. Soc. 1992; 114: 5269
• 8c Sato N, Matsuura T. J. Chem. Soc., Perkin Trans. 1 1996; 2345
• 8d Fürstner A, Leitner A, Méndez M, Kraus H. J. Am. Chem. Soc. 2002; 124: 13856
• 8e Kuse M, Kondo N, Ohyabu Y, Isobe M. Tetrahedron 2004; 60: 835
• 8f Wipf P, Xiao J, Geib SJ. Adv. Synth. Catal. 2005; 347: 1605
• 8g Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
• 9a Leclerc J.-P, Fagnou K. Angew. Chem. Int. Ed. 2006; 45: 7781
• 9b Jeong JU, Dong X, Rahman A, Marquis RW. Tetrahedron Lett. 2010; 51: 974
• 10a Li M, Hwa R. Tetrahedron Lett. 2009; 50: 1478
• 10b Berman AM, Bergman RG, Ellman JA. J. Org. Chem. 2010; 75: 7863
• 11a Melzig L, Gavryushin A, Knochel P. Org. Lett. 2007; 9: 5529
• 11b Miki Y, Tsuzaki Y, Hibino H, Aoki Y. Synlett 2004; 2206
• 12 Ohta A, Masano S, Iwakura S, Tamura A, Watahiki H, Tsutsui M, Akita Y, Watanabe T. J. Heterocycl. Chem. 1982; 19: 465
• 13 Tota YA, Elderfield RC. J. Org. Chem. 1942; 7: 313
• 14a Jones RG. J. Am. Chem. Soc. 1949; 71: 78
• 14b Karmas G, Spoerri PE. J. Am. Chem. Soc. 1952; 74: 1580
• 15 Simpson RF, Capone DL, Sefton MA. J. Agric. Food Chem. 2004; 52: 5425
• 16a Tamao K, Kiso Y, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 9268
• 16b Negishi E.-i. J. Organomet. Chem. 1999; 576: 179
• 16c Wang H, Liu J, Deng Y, Min T, Yu G, Wu X, Yang Z, Lei A. Chem.–Eur. J. 2009; 15: 1499
• 17 Erdik E, Koçoğlu M. Appl. Organomet. Chem. 2006; 20: 290