Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles

Tetrahedron Letters

Volumn 49, Issue 26, 2008, Pages 4138-4141

  Hong, Seong Jin ^a   Jeong, Seung Doo ^a   Yoo, Jaeduk ^a   Kim, Jong Seung ^b   Yoon, Juyoung ^c   Lee, Chang Hee ^a  

^a Kangwon National University   (South Korea)

^b Korea University   (South Korea)

^c Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 VINYLTHIOPHENE; 2,5 DIVINYL THIOPHENE; BENZENE DERIVATIVE; LEWIS ACID; PORPHYRIN DERIVATIVE; PYRROLE; THIOPHENE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; SYNTHESIS;

EID: 44149119018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.119     Document Type: Article

References (23)

1. Lee C.H., and Lindsey J.S. Tetrahedron 50 (1994) 11427-11440
2. Hammel D., Erk P., Seliuler B., Heinze J., and Mullen K. Adv. Mater. 4 (1992) 737
3. Vigmond S.J., Kallury K.M.R., and Thompson M. Anal. Chem. 64 (1992) 2763
4. Gryko D., and Lindsey J.S. J. Org. Chem. 65 (2000) 2249
5. Bruckner C., Sternberg E.D., Boyle R.W., and Dolphin D. Chem. Commun. (1997) 1689
6. Boyle R.W., Bruckner C., Posakony J., James B.R., and Dolphin D. Org. Synth. 76 (1999) 287
7. Bruckner C., Posakony J.J., Johnson C.K., Boyle R.W., James B.R., and Dolphin D. J. Porphyrins Phthalocyanines 2 (1998) 455
8. Wijesekera T.P. Can. J. Chem. 74 (1996) 1868
9. Casiraghi G., Cornia M., Zanardi F., Rassu G., Ragg E., and Bortolini R. J. Org. Chem. 59 (1994) 1801-1808
10. Boyle R.W., Xie L.Y., and Dolphin D. Tetrahedron Lett. 35 (1994) 5377-5380
11. Mizutani T., Ema T., Tomita T., Kuroda Y., and Ogoshi H. J. Am. Chem. Soc. 116 (1994) 4240-4250
12. Vigmond S.J., Chang M.C., Kallury K.M.R., and Thompson M. Tetrahedron Lett. 35 (1994) 2455-2458
13. Nishino N., Wagner R.W., and Lindsey J.S. J. Org. Chem. 61 (1996) 7534-7544
14. Laha J.K., Dhanalekshmi S., Taniguchi M., Ambroise A., and Lindsey J.S. Org. Process Res. Dev. 7 (2003) 799-812
15. Littler B.J., Miller M.A., Hung C.H., Wagner R.W., O'Shea D.F., Boyle P.D., and Lindsey J.S. J. Org. Chem. 64 (1999) 1391-1396
16. Temelli B., and Unaleroglu C. Tetrahedron 62 (2006) 10130-10135
17. Jeong S.D., Hong S.J., Park K.J., Ham S., Sessler J.L., and Lynch V. J. Org. Chem. 72 (2007) 6232-6240
18. Sim E.K., Jeong S.D., Yoon D.W., Hong S.J., Kang Y., and Lee C.H. Org. Lett. 8 (2006) 3355-3358
19. Kusurkar R.S., Nayak S.K., and Chavan N.L. Tetrahedron Lett. 47 (2006) 7323-7326
20. Hong S.J., Lee M.H., and Lee C.H. Bull. Korean Chem. Soc. 25 (2004) 1545-1550
21. Won D.H., and Lee C.H. Tetrahedron Lett. 44 (2003) 6695-6697
22. Liu Z., Yasseri A.A., Loewe R.S., Lysenko A.B., Malinovskii V.L., Zhao Q., Surthi S., Li Q., Misra V., Lindsey J.S., and Bocian D.F. J. Org. Chem. 69 (2004) 5568-5577
23. 3 (50 mL), water and dried with anhydrous sodium sulfate. After the drying agent was filtered off, the solvent was evaporated under reduced pressure.