Synthesis 2016; 48(13): 1974-1992
DOI: 10.1055/s-0035-1561974
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Uses of Kröhnke Methodology: A Short Survey

I. Sasaki*
a   CNRS; LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, 31077 Toulouse, France
b   Université de Toulouse; UPS, INP, LCC, 31077 Toulouse, France   Email: sasaki@lcc-toulouse.fr
› Author Affiliations
Further Information

Publication History

Received: 07 February 2016

Accepted after revision: 03 March 2016

Publication Date:
09 May 2016 (online)


Abstract

The scope of this short review is to point out how such an old reaction as the Kröhnke-type ring closure is still used nowadays to enable simple access to pyridines or polypyridines. Besides the usual Stille or Suzuki coupling reactions, which deal, respectively, with stannylated derivatives or boronic derivatives, the Kröhnke reaction can reach its target molecules with commercially available starting materials in a simple reaction medium without any special care.

1 Introduction

2 The Kröhnke Reaction

3 Applications

3.1 Catalysis

3.2 Materials

3.2.1 Dye-Sensitized Solar Cells

3.2.2 OLEDs and LECs

3.3 Biological Applications

3.3.1 Luminescent Probes

3.3.2 Chemosensors

3.3.3 Anticancer Compounds

3.3.4 Antimicrobial Activity

4 Miscellaneous

5 Summary and Outlook

 
  • References

  • 1 Kröhnke F, Zecher W. Angew. Chem. 1962; 74: 811 ; Angew. Chem. Int. Ed., 1962, 1, 626
  • 2 Kröhnke F. Synthesis 1976; 1
  • 3 Allais C, Graasot JM, Rodriguez J, Constantieux T. Chem. Rev. 2014; 114: 10829
  • 4 Hill MD. Chem. Eur. J. 2010; 16: 12052
  • 5 Kaes C, Katz A, Hosseini MW. Chem. Rev. 2000; 100: 3553
  • 6 Newkome GR, Patri AK, Holder E, Schubert US. Eur. J. Org. Chem. 2004; 235
    • 7a Wild A, Winter A, Schlütter F, Schubert US. Chem. Soc. Rev. 2011; 40: 1459
    • 7b Winter A, Hager MD, Newkome GR, Schubert US. Adv. Mater. 2011; 23: 5728
    • 7c Winter A, Hoeppener S, Newkome GR, Schubert US. Adv. Mater. 2011; 23: 3484
    • 8a Husson J, Knorr M. J. Heterocycl. Chem. 2012; 49: 452
    • 8b Husson J, Knorr M. Beilstein J. Org. Chem. 2012; 8: 379
  • 9 Hildebrandt A, Wetzold N, Ecorchard P, Walfort B, Rüffer T, Lang H. Eur. J. Inorg. Chem. 2010; 3615
    • 10a Hayoz P, von Zelewsky A. Tetrahedron Lett. 1992; 33: 5165
    • 10b Hayoz P, von Zelewsky A, Stoeckli-Evans H. J. Am. Chem. Soc. 1993; 115: 5111
  • 11 Ziegler M, Monney V, Stoeckli-Evans H, Von Zelewsky A, Sasaki I, Dupic G, Daran JC, Balavoine GG. A. J. Chem. Soc., Dalton Trans. 1999; 667
  • 12 Yeung CT, Lee WS, Tsang CS, Yiu SM, Wong WT, Wong WY, Kwong HL. Polyhedron 2010; 29: 1497
  • 13 Schmitz C, Leitner W, Franciò G. Eur. J. Org. Chem. 2015; 2889
  • 14 Malkov AV, Stoncius S, Bell M, Castelluzzo F, Ramirez-Lopez P, Biedermannova L, Langer V, Rulisek L, Kocovsky P. Chem. Eur. J. 2013; 19: 9167
  • 15 Chen X, Chen W, Wang L, Yu XQ, Huang DS, Pu L. Tetrahedron 2010; 66: 1990
  • 16 Ward TR. Acc. Chem. Res. 2011; 44: 47
  • 17 Bos J, Fusetti F, Driessen AJ. M, Roelfes G. Angew. Chem. Int. Ed. 2012; 51: 7472
  • 18 O’Regan B, Grätzel M. Nature 1991; 353: 737
  • 19 Hagfeldt A, Boschloo G, Sun L, Kloo L, Pettersson H. Chem. Rev. 2010; 110: 6595
  • 20 Kimura M, Masuo J, Tohata Y, Obuchi K, Masaki N, Murakami TN, Koumura N, Hara K, Fukui A, Yamanaka R, Mori S. Chem. Eur. J. 2013; 19: 1028
  • 21 Chan HT, Mak CS. K, Djurisic AB, Chan WK. Macromol. Chem. Phys. 2011; 212: 774
    • 22a Wadman SH, Kroon JM, Bakker K, Lutz M, Spek AL, van Klink GP. M, van Koten G. Chem. Commun. 2007; 1907
    • 22b Wadman SH, Kroon JM, Bakker K, Havenith RW. A, van Klink GP. M, van Koten G. Organometallics 2010; 29: 1569
  • 23 Wadman SH, van Leeuwen YM, Havenith RW. A, van Klink GP. M, van Koten G. Organometallics 2010; 29: 5635
  • 24 Wadman SH, Tooke DM, Spek AL, van Klink GP. M, van Koten G. Inorg. Chim. Acta 2010; 363: 1701
    • 25a Robson KC. D, Sporinova B, Koivisto BD, Schott E, Brown DG, Berlinguette CP. Inorg. Chem. 2011; 50: 6019
    • 25b Muise SS. R, Severin HA, Koivisto BD, Robson KC. D, Schott E, Berlinguette CP. Organometallics 2011; 30: 6628
  • 26 Hu K, Severin HA, Koivisto BD, Robson KD. C. D, Schott E, Arratia-Perez R, Meyer GJ, Berlinguette CP. J. Phys. Chem. C 2014; 118: 17079
  • 27 Bozic-Weber B, Brauchli SY, Constable EC, Fürer SO, Housecroft CE, Malzner FJ, Wright IA, Zampese JA. Dalton Trans. 2013; 42: 12293
  • 28 Malzner FJ, Brauchli SY, Constable EC, Housecroft CE, Neuburger M. RCS Adv. 2014; 4: 48712
  • 29 Bozic-Weber B, Brauchli SY, Constable EC, Fürer SO, Housecroft CE, Wright IA. Phys. Chem. Chem. Phys. 2013; 15: 4500
  • 30 Woodward CP, Coghlan CJ, Rüther T, Jones TW, Hebting Y, Cordiner RL, Dawson RE, Robinson DE. J E, Wilson GJ. Tetrahedron 2015; 71: 5238
  • 31 Bozic-Weber B, Constable EC, Housecroft CE. Coord. Chem. Rev. 2013; 257: 3089
  • 32 Saccone D, Magistris C, Barbero N, Quagliotto P, Barolo C, Viscardi G. Materials 2016; 9: 137
  • 33 Higuchi M. J. Mater. Chem. C 2014; 2: 9331
  • 34 Wu KQ, Guo J, Yan JF, Xie LL, Xu FB, Bai S, Nockemann P, Yuan YF. Organometallics 2011; 30: 3504
  • 35 Yuen MY, Low KH, Kwok CC, Chui SS. Y, Ma CW, Zhu N, Che CM. Chem. Eur. J. 2010; 16: 14131
  • 36 Chow PK, Cheng G, Tong GS. M, To WP, Kwong WL, Low KH, Kwok CC, Ma C, Che CM. Angew. Chem. Int. Ed. 2015; 54: 2084
  • 37 Kui SC. F, Hung FF, Lai SL, Yuen MY, Kwok CC, Low KH, Chu SS. Y, Che CM. Chem. Eur. J. 2012; 18: 96
  • 38 Kui SC. F, Chow PK, Tong GS. M, Lai SL, Cheng G, Kwok CC, Low KH, Ko MY, Che CM. Chem. Eur. J. 2013; 19: 69
  • 39 Chow PK, Cheng G, Tong GS. M, To WP, Kwong WL, Low KH, Kwok CC, Ma C, Che CM. Angew. Chem. Int. Ed. 2013; 52: 11775
  • 40 Au VK. M, Lam WH, Wong WT, Yam VW. W. Inorg. Chem. 2012; 51: 7537
  • 41 Au VK. M, Tsang DP. K, Wong KM. C, Chan MY, Zhu N, Yam VW. W. Inorg. Chem. 2013; 52: 12713
  • 42 Constable EC, Housecroft CE, Kopecky P, Martin CJ, Wright IA, Zampese JA, Bolink HJ, Pertegas A. Dalton Trans. 2013; 42: 8086
  • 43 Elmes RB. P, Erby M, Bright SA, Williams DC, Gunnlaugsson T. Chem. Commun. 2012; 48: 2588
  • 44 He G, Zhao L, Chen K, Liu Y, Zhu H. Talanta 2013; 106: 73
  • 45 Ye Z, Song B, Yin Y, Zhang R, Yuan J. Dalton Trans. 2013; 42: 14380
  • 46 Wu D, Shao T, Men J, Chen X, Gao G. Dalton Trans. 2014; 43: 1753
  • 47 Trigo-López M, Muñoz A, Ibeas S, Serna F, García FC, García JM. Sens. Actuators, B 2016; 226: 118
  • 48 Betti M, Castagnoli G, Panico A, Coccone SS, Wiedenau P. Org. Process Res. Dev. 2012; 16: 1739
    • 49a Thapa P, Karki R, Yun M, Kadayat TM, Lee E, Kwon HB, Na Y, Cho WJ, Kim ND, Jeong BS, Kwon Y, Lee ES. Eur. J. Med. Chem. 2012; 52: 123
    • 49b Karki R, Thapa P, Yoo HY, Kadayat TM, Park PH, Na Y, Lee E, Jeon KH, Cho WJ, Choi H, Kwon Y, Lee ES. Eur. J. Med. Chem. 2012; 49: 219
  • 50 Thapa P, Lee ES. Bull. Korean Chem. Soc. 2012; 13: 5-1769
  • 51 Thapa P, Karki R, Yoo HY, Park PH, Lee E, Jeon KH, Na Y, Cho WJ, Kwon Y, Lee ES. Bioorg. Chem. 2012; 40: 67
    • 52a Thapa U, Thapa P, Karki R, Yun M, Choi JH, Jahng Y, Lee E, Jeon KH, Na Y, Ha EM, Cho WJ, Kwon Y, Lee ES. Eur. J. Med. Chem. 2011; 46: 3201
    • 52b Kwon HB, Park C, Jeon KH, Lee E, Park SE, Jun KY, Kadayat TM, Thapa P, Karki R, Na Y, Park MS, Rho SB, Lee ES, Kwon Y. J. Med. Chem. 2015; 58: 1100
  • 53 Kadayat TM, Park C, Jun KY, Bahadur T, Magar T, Bist G, Yoo HY, Kwon Y, Lee ES. Eur. J. Med. Chem. 2015; 90: 302
  • 54 Sun RW.-Y, Chow LF, Li XH, Yan JJ, Chui SS. Y, Che CM. Chem. Sci. 2011; 2: 728
  • 55 Wang P, Leung CH, Ma DL, Sun RW. Y, Yan SC, Chen QS, Che CM. Angew. Chem. Int. Ed. 2011; 50: 2554
  • 56 Zou T, Liu J, Lum CT, Ma C, Chan RC. T, Lok CN, Kwok WM, Che CM. Angew. Chem. Int. Ed. 2014; 53: 10119
  • 57 Patel MN, Patel CR, Joshi HN, Vekariya PA. Appl. Biochem. Biotechnol. 2014; 172: 1846
    • 58a Patel MN, Parmar PA, Gandhi DS, Patidar AP. Spectrochim. Acta, Part A 2012; 97: 54
    • 58b Patel M, Gandhi DS, Parmar PA, Bhatt BS, Patidar AP. Z. Anorg. Allg. Chem. 2012; 638: 838
  • 59 Patel AK, Patel NH, Patel MA, Brahmbhatt DI. J. Heterocycl. Chem. 2012; 49: 504
    • 60a Patel MN, Bhatt BS, Dosi PA, Amaravady NV. R L, Movaliya HV. Appl. Organomet. Chem. 2012; 26: 217
    • 60b Patel MN, Bhatt BS, Dosi PA. Z. Anorg. Allg. Chem. 2012; 638: 152
  • 61 Shu WM, Ma JR, Yang Y, Wu AX. Org. Lett. 2014; 16: 1286
  • 62 Gogoi S, Dutta M, Gogoi J, Boruha RC. Tetrahedron Lett. 2011; 52: 813
  • 63 Prasanna P, Balamurugan K, Perumal S, Menéndez JC. Green Chem. 2011; 13: 2123
  • 64 Sieling U, Vor der Brüggen J, Vorfeld U, Stammler A, Stammler HG. Z. Naturforsch., B 2003; 58: 443
    • 65a Tu S, Jia R, Jiang B, Zhang J, Zhang Y, Yao C, Ji S. Tetrahedron 2007; 63: 381
    • 65b Sasaki I, Daran JC, Comenges G. Beilstein J. Org. Chem. 2015; 11: 1781