Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties

KÜÇÜKBAY, HASAN; YILMAZ, ÜLKÜ; BUĞDAY, Nesrin; YAVUZ, Kemal

Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties

HASAN KÜÇÜKBAY, (İnönü Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Malatya, Türkiye)

Ülkü YILMAZ, (İnönü Üniversitesi, Battalgazi Meslek Yüksek Okulu Malatya, Türkiye)

Kemal YAVUZ, (İnönü Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Malatya, Türkiye)

Nesrin BUĞDAY (İnönü Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Malatya, Türkiye)

Turkish Journal of Chemistry

4 0

Yıl: 2015 Cilt: 39 Sayı: 6 Sayfa Aralığı: 1265 - 1278 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties

Öz:

Five novel benzimidazole salts ( 1 { 5 ) having N-phthalimidoethyl and 4-substituted benzyl were synthesized and identi ed by 1 H NMR, 13 C NMR, and IR spectroscopic methods and microanalysis. A mixture of the benzimidazole salts ( 1 { 5 ), Pd(OAc) 2 , and K 2 CO 3 in DMF-H 2 O catalyzed, in high yield, the Suzuki{Miyaura and the Heck{Mizoroki cross-coupling reactions assisted by microwave irradiation in 5 min. The novel benzimidazole salts ( 1 { 5 ), Pd(OAc) 2 , Cs 2 CO 3 , PEG, and Cu nanoparticles catalyzed, in high yield, the Sonogashira coupling reaction promoted by microwave irradiation in 10 min. The same benzimidazole salts ( 1 { 5 ), Pd(OAc) 2 , Cs 2 CO 3 , and TBAB catalyzed, in moderate or low yield, the Buchwald{Hartwig reaction assisted by microwave irradiation in 60 min. The efficiency of the catalyst system in these four reactions was discussed as well as the electron-releasing and withdrawing substituent effects on the benzimidazole ligands.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Mehta, V. P.; Van der Eycken, E. Chem. Soc. Rev. 2011 , 40 , 4925{4936.
2. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis ; Wiley-VCH: Weinheim, Germany, 2004.
3. Yin, L.; Liebscher, J. Chem. Rev. 2007 , 107 , 133{173.
4. Linninger, C. S.; Herdtweck, E.; Hoffmann, S. D.; Herrmann, W. A.; Kuhn, F. E. J. Mol. Struc. 2008 , 890 , 192{197.
5. Marion, N.; Nolan, S. P. Accont. Res. 2008 , 41 , 1440{1449.
6. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice ; Oxford University Press, New York, NY, USA, 1998.
7. Kappe, C. O. Angew. Chem. Int. Ed. 2004 , 43 , 6250{6284.
8. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002 , 35 , 717{727.
9. Suzuki, A. J. Organomet. Chem. 1999 , 576 , 147{168.
10. Heck, R. F. Acc. Chem. Res. 1979 , 12 , 146{151.
11. Miyaura, N.; Suzuki, A. Chem. Rev. 1995 , 95 , 2457{2483.
12. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995 , 28 , 2{7.
13. Suzuki, A. ChemComm. 2005 , 4759{4763.
14. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000 , 100 , 3009{3066.
15. Miyaura, N. Top. Curr. Chem. 2002 , 219 , 11{59.
16. Heck, R. F. Synlett 2006 , 2855{2860.
17. Akba, O.; Durap, F.; Aydemir, M.; Baysal, A.; Gumgum, B.; Ozkar, S. J. Organomet. Chem. 2009 , 694 , 731{736.
18. Leadbeater, N. E.; Marco, M. Org. Lett. 2002 , 4 , 2973{2976.
19. Dawood, K. M. Tetrahedron 2007 , 63 , 9642{9651.
20. Astruc, D. Inorg. Chem. 2007 , 46 , 1884{1894.
21. Prokopcova, H.; Ramirez, J.; Fernandez, E.; Kappe, C. O. Tetrahedron Lett. 2008 , 49 , 4831{4835.
22. Martinez, A. V.; Invernizzi, F.; Leal-Duaso, A.; Mayoral, J. A.; Garcia, J. I. RSC Adv. 2015 , 5 , 10102{10109.
23. Yin, L.; Liebscher, J. Chem. Rev . 2007 , 107 , 133{173.
24. Tudose, A.; Delaude, L.; Andre, B.; Demonceau, A. Tetrahedron Lett. 2006 , 47 , 8529{8533.
25. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. 2007 , 46 , 2768{2813.
26. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975 , 16 , 4467{4470.
27. Sonogashira, K. J. Organomet. Chem. 2002 , 653 , 46{49.
28. Thomas, A. M.; Sujatha, A.; Anilkumar, G. RSC Adv. 2014 , 4 , 21688{21698.
29. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. Int. E. 1995 , 34 , 1348{1350.
30. Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995 , 36 , 3609{3612.
31. Hartwig, J. F. Angew. Chem. Int. Ed. 1998 , 37 , 2046{2067.
32. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002 , 219 , 131{209.
33. Larhed, M.; Hallberg, A. J. Org. Chem. 1996 , 61 , 9582{9584.
34. Mercan, D.; Cetinkaya, E.; Cetinkaya, B. J. Organomet. Chem. 2011 , 696 , 1359{1366.
35. Mohanty, S.; Suresh, D.; Balakrishna, M. S.; Mague, J. T. Tetrahedron 2008 , 64 , 240{ 247.
36. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008 , 64 , 3047{3101.
37. Mehta, V. P.; Appukkuttan, P.; Van der Eycken, E. Curr. Org. Chem. 2011 , 15 , 265{283.
38. Beletskaya, I.; Tyurin, V. Molecules 2010 , 15 , 4792{4814.
39. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002 , 41 , 4176{4211.
40. Appukkuttan, P.; Van der Eycken, E. Eur. J. Org. Chem. 2008 , 1133{1155.
41. Kucukbay, H.; Sireci, N.; Ylmaz, U.; Deniz, S.; Akkurt, M.; Baktr, Z.; Buyukgungor, O. Turk. J. Chem. 2012 , 36 , 201{217.
42. Nolan, S. P. N-Heterocyclic Carbenes in Synthesis ; Wiley-VCH: Weinheim, Germany, 2006.
43. Colacot, T. New Trends in Cross-Couplings: Theory and Applications ; RSC: London, UK, 2014.
44. Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann W. A. Angew. Chem. Int. Ed . 2002 , 41 , 1363{1365.
45. Selvrakumar, K.; Zagf, Sponnanberg, M.; Beller, M. Chem. Eur. J. 2002 , 8 , 3901{3906.
46. Culkin, D. A.; Hartwig, J. F. Organometallics 2004 , 23 , 3398{3416.
47. Lebel, H.; Jonas, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004 , 126 , 5046{5047.
48. Paczol, A.; Benyer, A. C.; Kotschy, A. J. Org. Chem. 2006 , 71 , 5969{5979.
49. Ozdemir, _ I.; Demir, S.; Gurbuz, N.; Cetinkaya, B.; Toupet, L.; Bruneau, C.; Dixneuf, P. H. Eur. J. Inorg. Chem. 2009 , 1942{1949.
50. Ylmaz, U.; Sireci, N.; Deniz, S.; Kucukbay, H. Appl. Organomet. Chem. 2010 , 24 , 414{420.
51. Kucukbay, H.; Sireci, N.; Ylmaz, U.; Akkurt, M.; Yalcn, S. P.; Tahir, M. N.; Ott, H. Appl. Organomet. Chem. 2011 , 25 , 255{261.
52. Ylmaz, U.; Kucukbay, H.; Sireci, N.; Akkurt, M.; Gunal, S.; Durmaz, R.; Tahir, M. N. Appl. Organomet. Chem. 2011 , 25 , 366{373.
53. Ylmaz, U.; Kucukbay, H.; Turktekin, C. S.; Akkurt, M.; Buyukgungor, O. Turk. J. Chem. 2013 , 37 , 721{733.
54. Zeni, G.; Larock, R. C. Chem. Rev. 2006 , 106 , 4644{4680.
55. Sabounvhei, S. J.; Ahmadi, M. Catal. Commun. 2013 , 37 , 114{121.
56. Cao, X.; Yu, F.; Li, L.; Yao, Z.; Xie, Y. J. Cryst. Growth. 2003 , 254 , 164{168.
57. Wang, Y.; Biradar, A. V.; Wang, G.; Sharma, K. K.; Duncan, C. T., Rangan, S.; Asefa, T. Chem. Eur. J. 2010 , 16 , 10735{10743.
58. Hartwig, J. F. Acc. Chem. Res. 2008 , 41 , 1534{1544.
59. Fors, B. P., Buchwald, S. L. J. Am. Chem. Soc . 2010 , 132 , 15914{15917.
60. Wan, Y.; Wallinder, C.; Plouffe, B.; Beaudry, H.; Mahalingam, A. K.; Wu, X.; Johansson, B.; Holm, M.; Botoros, M.; Karlen, A.; et al. J. Med. Chem. 2004 , 47 , 5995{6008.
61. Xia, Q. Q.; Chen, W. Z.; Qiu, H. Y.; Direct, C. N. J. Org. Chem. 2011 , 76 , 7577{7582.
62. Nikitenko, A. A.; Kha zova, G.; Gross, J. L. PCT Int. Appl. 2010 , WO 20100009029 , A2 2010121.
63. Filipskikh, T. P.; Pozharskii, A. F.; Koroleva, V. N.; Simonov, A. M.; Zvezdina, E. A. Khim. Geterotsikl. Soedin . 1972 , 6 , 809{811.
64. Yang, Q.; Wang, Y.; Lin, D.; Zhang, M. Tetrahedron Lett. 2013 , 54 , 1994{1997.

APA	KÜÇÜKBAY H, YILMAZ Ü, YAVUZ K, BUĞDAY N (2015). Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. , 1265 - 1278.
Chicago	KÜÇÜKBAY HASAN,YILMAZ ÜLKÜ,YAVUZ Kemal,BUĞDAY Nesrin Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. (2015): 1265 - 1278.
MLA	KÜÇÜKBAY HASAN,YILMAZ ÜLKÜ,YAVUZ Kemal,BUĞDAY Nesrin Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. , 2015, ss.1265 - 1278.
AMA	KÜÇÜKBAY H,YILMAZ Ü,YAVUZ K,BUĞDAY N Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. . 2015; 1265 - 1278.
Vancouver	KÜÇÜKBAY H,YILMAZ Ü,YAVUZ K,BUĞDAY N Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. . 2015; 1265 - 1278.
IEEE	KÜÇÜKBAY H,YILMAZ Ü,YAVUZ K,BUĞDAY N "Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties." , ss.1265 - 1278, 2015.
ISNAD	KÜÇÜKBAY, HASAN vd. "Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties". (2015), 1265-1278.

APA	KÜÇÜKBAY H, YILMAZ Ü, YAVUZ K, BUĞDAY N (2015). Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. Turkish Journal of Chemistry, 39(6), 1265 - 1278.
Chicago	KÜÇÜKBAY HASAN,YILMAZ ÜLKÜ,YAVUZ Kemal,BUĞDAY Nesrin Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. Turkish Journal of Chemistry 39, no.6 (2015): 1265 - 1278.
MLA	KÜÇÜKBAY HASAN,YILMAZ ÜLKÜ,YAVUZ Kemal,BUĞDAY Nesrin Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. Turkish Journal of Chemistry, vol.39, no.6, 2015, ss.1265 - 1278.
AMA	KÜÇÜKBAY H,YILMAZ Ü,YAVUZ K,BUĞDAY N Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. Turkish Journal of Chemistry. 2015; 39(6): 1265 - 1278.
Vancouver	KÜÇÜKBAY H,YILMAZ Ü,YAVUZ K,BUĞDAY N Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties. Turkish Journal of Chemistry. 2015; 39(6): 1265 - 1278.
IEEE	KÜÇÜKBAY H,YILMAZ Ü,YAVUZ K,BUĞDAY N "Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties." Turkish Journal of Chemistry, 39, ss.1265 - 1278, 2015.
ISNAD	KÜÇÜKBAY, HASAN vd. "Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald{Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties". Turkish Journal of Chemistry 39/6 (2015), 1265-1278.