Synthesis 2014; 46(15): 2051-2056
DOI: 10.1055/s-0033-1341265
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Dihydropyrrole Derivatives by a Palladium-Catalyzed Heck and Suzuki Cross-Coupling Cascade Reaction

Jinsong Peng*
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
b   Post-Doctoral Mobile Research Station of Forestry Engineering, Northeast Forestry University, Harbin, 150040, P. R. of China
,
Yan Zhao
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
,
Jingjie Zhou
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
,
Yuehang Ding
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
,
Chunxia Chen*
a   Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, P. R. of China   Fax: +86(451)82190679   eMail: jspeng1998@nefu.edu.cn   eMail: 080122@nefu.edu.cn
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 16. Januar 2014

Accepted after revision: 31. März 2014

Publikationsdatum:
13. Mai 2014 (online)


Abstract

An expedient protocol for the synthesis of 5-aryl-2,3-dihydropyrroles, starting from N-tosyl-protected 2-methylprop-2-en-1-amine, alkynyl bromides, and arylboronic acids, is described. The sequential reaction sequence involves nucleophilic addition of the sulfonamide to the alkynyl bromide, followed by a palladium-catalyzed tandem intramolecular Heck and intermolecular Suzuki cross-coupling reaction of the bromoalkene adduct.

Supporting Information

 
  • References

    • 1a Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
    • 1b Humphrey JM, Liao Y, Ali A, Rein T, Wong Y.-L, Chen H.-J, Courtney AK, Martin SF. J. Am. Chem. Soc. 2002; 124: 8584
    • 1c Herzon SB, Myers AG. J. Am. Chem. Soc. 2005; 127: 5342
    • 1d Martin R, Jäger A, Böhl M, Richter S, Fedorov R, Manstein DJ, Gutzeit HO, Knölker H.-J. Angew. Chem. Int. Ed. 2009; 48: 8042
    • 1e Wegner J, Ley SV, Kirschning A, Hansen A.-L, Garcia JM, Baxendale IR. Org. Lett. 2012; 14: 696
  • 2 Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
  • 3 Smela E. Adv. Mater. (Weinheim, Ger.) 2003; 15: 481
  • 4 Castellano S, Fiji HD. G, Kinderman SS, Watanabe M, Leon P, Tamanoi F, Kwon O. J. Am. Chem. Soc. 2007; 129: 5843
  • 5 Magedov IV, Luchetti G, Evdokimov NM, Manpadi M, Steelant WF. A, Van slambrouck S, Tongwa P, Antipin MY, Kornienko A. Bioorg. Med. Chem. Lett. 2008; 18: 1392
  • 6 Cox CD, Coleman PJ, Breslin MJ, Whitman DB, Garbaccio RM, Fraley ME, Buser CA, Walsh ES, Hamilton K, Schaber MD, Lobell RB, Tao W, Davide JP, Diehl RE, Abrams MT, South VJ, Huber HE, Torrent M, Prueksaritanont T, Li C, Slaughter DE, Mahan E, Fernandez-Metzler C, Yan Y, Kuo LC, Kohl NE, Hartman GD. J. Med. Chem. 2008; 51: 4239
    • 7a Zhu W, Cai G, Ma D. Org. Lett. 2005; 7: 5545
    • 7b Guo C, Xue M.-X, Zhu M.-K, Gong L.-Z. Angew. Chem. Int. Ed. 2008; 47: 3414
    • 7c Wender PA, Strand D. J. Am. Chem. Soc. 2009; 131: 7528
    • 7d Brawn RA, Panek JS. Org. Lett. 2009; 11: 473
    • 7e Fan J, Gao L, Wang Z. Chem. Commun. 2009; 45: 5021
    • 7f Tian J, Zhou R, Sun H, Song H, He Z. J. Org. Chem. 2011; 76: 2374
    • 7g Liu C.-R, Zhu B.-H, Zheng J.-C, Sun X.-L, Xie Z, Tang Y. Chem. Commun. 2011; 47: 1342
    • 8a Ma S, Gao W. Org. Lett. 2002; 4: 2989
    • 8b Monge D, Jensen KL, Franke PT, Lykke L, Jørgensen KA. Chem. Eur. J. 2010; 16: 9478
    • 8c Cheng J, Jiang X, Zhu C, Ma S. Adv. Synth. Catal. 2011; 353: 1676
    • 8d Zhang G, Zhang Y, Jiang X, Yan W, Wang R. Org. Lett. 2011; 13: 3806
    • 8e Polindara-García LA, Miranda LD. Org. Lett. 2012; 14: 5408
    • 8f Miura T, Tanaka T, Hiraga K, Stewart SG, Murakami M. J. Am. Chem. Soc. 2013; 135: 13652
    • 8g Ghorai MK, Tiwari DP. J. Org. Chem. 2013; 78: 2617
  • 9 Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Rutjes FP. J. T. Org. Lett. 2001; 3: 2045
  • 10 Feldman KS, Bruendl MM, Schildknegt K, Bohnstedt AC. J. Org. Chem. 1996; 61: 5440
  • 11 Ma S, Yu F, Li J, Gao W. Chem. Eur. J. 2007; 13: 247
  • 12 Zhou X, Zhang H, Yuan J, Mai L, Li Y. Tetrahedron Lett. 2007; 48: 7236
  • 13 Ding C.-H, Dai L.-X, Hou X.-L. Tetrahedron 2005; 61: 9586
  • 14 Wurz RP, Charette AB. Org. Lett. 2005; 7: 2313
    • 15a Tietze LF. Chem. Rev. 1996; 96: 115
    • 15b Negishi E, Copéret C, Ma S, Liou S.-Y, Liu F. Chem. Rev. 1996; 96: 365
    • 15c Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644
    • 15d Ohno H. Asian J. Org. Chem. 2013; 2: 18
    • 15e Muzart J. Tetrahedron 2013; 69: 6735
    • 16a Yamagishi M, Nishigai K, Hata T, Urabe H. Org. Lett. 2011; 13: 4873
    • 16b Wang S, Li P, Yu L, Wang L. Org. Lett. 2011; 13: 5968
    • 16c Chen Z, Huang G, Jiang H, Huang H, Pan X. J. Org. Chem. 2011; 76: 1134
    • 16d Li Y, Zhao J, Chen H, Liu B, Jiang H. Chem. Commun. 2012; 48: 3545
    • 16e Yamagishi M, Nishigai K, Ishii A, Hata T, Urabe H. Angew. Chem. Int. Ed. 2012; 51: 6471
    • 16f Liu B, Li Y, Yin M, Wu W, Jiang H. Chem. Commun. 2012; 48: 11446
    • 16g Peng J, Shang G, Chen C, Miao Z, Li B. J. Org. Chem. 2013; 78: 1242
  • 17 Grigg R, Dorrity MJ, Malone JF, Sridharan V, Sukirthalingam S. Tetrahedron Lett. 1990; 31: 1343
  • 18 Lafrance M, Fagnou K. J. Am. Chem. Soc. 2006; 128: 16496
  • 19 Billingsley KL, Anderson KW, Buchwald SL. Angew. Chem. Int. Ed. 2006; 45: 3484