2,6-Bis(phenylethynyl)biphenyls and Their Cyclization to Pyrenes

Abstract

We present a new protocol for pyrene synthesis via transition-metal cross-couplings. The initially prepared 2,6-bis(phenylethynyl)biphenyls were transformed to pyrenes with uncommon 4,10-disubstitution through an electrophilic cyclization. The precursors were synthesized by Suzuki–Miyaura cross-coupling, which provides 2,6-dibromobiphenyls; these were subsequently coupled with phenylethynyl derivatives via Kumada cross-coupling.

Key words

alkynes - biaryls - pyrenes - cyclizations - transition metals­

• References

• 1a Tang CW. Appl. Phys. Lett. 1986; 48: 183
• 1b Sonar P, Soh MS, Cheng YH, Henssler JT, Sellinger A. Org. Lett. 2010; 12: 3292
• 1c Moorthy JN, Venkatakrishnan P, Natarajan P, Lin ZH, Chow TJ. J. Org. Chem. 2010; 75: 2599
• 1d Kim HM, Lee YO, Lim CS, Kim JS, Cho BR. J. Org. Chem. 2008; 73: 5127
• 1e Moorthy JN, Natarajan P, Venugopalan P. J. Org. Chem. 2009; 74: 8566
• 1f Hu JY, Era M, Elsegood MR. J, Yamato T. Eur. J. Org. Chem. 2010; 72
• 1g Tang CW, Vanslyke SA. Appl. Phys. Lett. 1987; 51: 913
• 1h Shirakawa H, Louis EJ, Macdiarmid AG, Chiang CK, Heeger AJ. J. Chem. Soc., Chem. Commun. 1977; 578
• 1i Chabinyc ML, Salleo A. Chem. Mater. 2004; 16: 4509
• 2 Moorthy JN, Natarajan P, Venkatakrishnan P, Huang DF, Chow TJ. Org. Lett. 2007; 9: 5215
• 3 Walker DB, Howgego J, Davis AP. Synthesis 2010; 3686
• 4 Müllen K, Figueira-Duarte T. Chem. Rev. 2011; 111: 7260
• 5a Zöphel L, Enkelmann V, Rieger R, Müllen K. Org. Lett. 2011; 13: 4506
• 5b Venkataramana G, Dongare P, Dawe LN, Thompson DW, Zhao YM, Bodwell GJ. Org. Lett. 2011; 13: 2240
• 5c Burdon J, Parsons IW, Gill HS. J. Chem. Soc., Perkin Trans. 1 1979; 1351
• 5d Bittermann H, Siegemund D, Malinovskii VL, Haner R. J. Am. Chem. Soc. 2008; 130: 15285
• 5e Mochida K, Kawasumi K, Segawa Y, Itami K. J. Am. Chem. Soc. 2011; 133: 10716
• 5f Lee YO, Pradhan T, No K, Kim JS. Tetrahedron 2012; 68: 1704
• 6 Schreiner PR, Prall M, Lutz V. Angew. Chem. Int. Ed. 2003; 42: 5757
• 7a Fürstner A, Mamane V. J. Org. Chem. 2002; 67: 6264
• 7b Goldfinger MB, Crawford KB, Swager TM. J. Am. Chem. Soc. 1997; 119: 4578
• 8 Mamane V, Hannen P, Fürstner A. Chem. Eur. J. 2004; 10: 4556
• 9 Mukherjee A, Pati K, Liu RS. J. Org. Chem. 2009; 74: 6311
• 10a Modrakowski C, Flores SC, Beinhoff M, Schluter AD. Synthesis 2001; 2143
• 10b Wang J, Ho L, Chen LH, Zhao Z, Zhao W, Qian XJ, Humala N, Seror I, Bartholomew S, Rosendorff C, Pasinetti GM. J. Clin. Invest. 2007; 117: 3393
• 10c Gray GW. Liq. Cryst. 1998; 24: 5
• 11 Palekar LD, Maruya KA, Kostka JE, Wiegel J. Chemosphere 2003; 53: 593
• 12a O’Brien CJ, Kantchev EA. B, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG. Chem. Eur. J. 2006; 12: 4743
• 12b Organ MG, Avola S, Dubovyk I, Hadei N, Kantchev EA. B, O’Brien CJ, Valente C. Chem. Eur. J. 2006; 12: 4749
• 13a Zhao Y, Truhlar DG. Acc. Chem. Res. 2008; 41: 157
• 13b Zhao Y, Truhlar DG. Theor. Chem. Acc. 2008; 120: 215
• 14 Sonogashira K. J. Organomet. Chem. 2002; 653: 46
• 15a Yao TL, Campo MA, Larock RC. J. Org. Chem. 2005; 70: 3511
• 15b Mehta S, Waldo JP, Larock RC. J. Org. Chem. 2009; 74: 1141
• 16 Yao TL, Campo MA, Larock RC. Org. Lett. 2004; 6: 2677
• 17a UV Atlas Organischer Verbindungen, Vol. III. Sandemann I, Perkampus HH. Verlag Chemie; Weinheim: 1966
• 17b Ferguson J, Reeves LW, Schneider WG. Can. J. Chem. 1957; 35: 1117
• 17c Kubat P, Civis S, Muck A, Barek J, Zima J. J. Photochem. Photobiol., A 2000; 132: 33
• 18a Malkina AG, Brandsma L, Vasilevsky SF, Trofimov BA. Synthesis 1996; 589
• 18b Coe JW, Wirtz MC, Bashore CG, Candler J. Org. Lett. 2004; 6: 1589
• 18c Morgan J, Pinhey JT. J. Chem. Soc., Perkin Trans. 1 1990; 715