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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 23
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Original Articles

C-C bond cleavage: Metal-free-catalyzed reaction of Betti bases with various heterocycles under microwave irradiation

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Pages 1940-1946 | Received 22 Aug 2016, Published online: 07 Oct 2016

References

  • Selected reviews and recent examples: (a) Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662; (b) Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 3124; (c) Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 3518; (d) Matsuda, T.; Shigeno, M.; Murakami, M. J. Am. Chem. Soc. 2007, 129, 12086; (e) Seiser, T.; Cramer, N. J. Am. Chem. Soc. 2010, 132, 5340; (f) Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006; (g) Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244; (h) Chen, K.; Li, H.; Lei, Z.-Q.; Li, Y.; Ye, W.-H.; Zhang, L.-S.; Sun, J.; Shi, Z.-J. Angew. Chem. Int. Ed. 2012, 51, 9851; (i) Ishida, N.; Masuda, Y.; Uemoto, S.; Murakami, M. Chem. Eur. J. 2016, 22, 6524; (j) Ge, S.; Chaładaj, W.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 4149.
  • (a) Murphy, S. K.; Park, J.-W.; Cruz, F. A.; Dong, V. M. Science 2015, 347, 56; (b) Matsuda, T.; Shigeno, M.; Makino, M.; Murakami, M. Org. Lett. 2006, 8, 3379; (c) Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862; (d) Wang, Y.; Kang, Q. Org. Lett. 2014, 16, 4190; (e) Zhu, Y.; Yan, H.; Lu, L.; Liu, D.; Rong, G.; Mao, J. J. Org. Chem. 2013, 78, 9898; (f) Fan, W.; Yang, Y.; Lei, J.; Jiang, Q.; Zhou, W. J. Org. Chem. 2015, 80, 8782.
  • (a) Allpress, C. J.; Berreau, L. M. Coord. Chem. Rev. 2013, 257, 3005; (b) Yoshimoto, F. K.; Auchus, R. J. J. Steroid Biochem. Mol. Biol. 2015, 151, 52; (c) Akhtar, M.; Wright, J. N.; Lee-Robichaud, P. J. Steroid Biochem. Mol. Biol. 2011, 125, 2; (d) Meyer, D.; Leifels, T.; Sbaragli, L.; Woggon, W.-D. Biochem. Biophys. Res. Commun. 2005, 338, 372.
  • (a) Guo, L.-N.; Deng, Z.-Q.; Wua, Y.; Hub, J. RSC Adv. 2016, 6, 27000; (b) Miao, C.-X.; Yu, B.; He, L.-N. Green Chem. 2011, 13, 541; (c) Liu, H.; Dong, C.; Zhang, Z.; Wu, P.; Jiang, X. Angew. Chem. Int. Ed. 2012, 51, 12570; (d) Kumar, A.; Shah, B. A. Org. Lett. 2015, 17, 5232; (e) Deb, M. L.; Bhuyan, P. J. Tetrahedron Lett. 2007, 48, 2159; (f) Deb, M. L.; Bhuyan, P. J. Synthesis 2008, 2891.
  • (a) Zarei, M.; Jarrahpour, A.; Ebrahimi, E.; Aye, M.; Badrabady, S. A. T. Tetrahedron 2012, 68, 5505; (b) Zarei, M.; Jarrahpour, A. Tetrahedron Lett. 2011, 52, 1192; (c) Azzena, U.; Carraro, M.; Meloni, C.; Murgia, I.; Pisano, L.; Pittalis, M.; Luisi, R.; Musio, B.; Degennaro, L. Tetrahedron: Asymmetry 2014, 25, 1550.
  • (a) Rehan, M.; Maity, S.; Morya, L. K.; Pal, K.; Ghorai, P. Angew. Chem. Int. Ed. 2016, 55, 7728; (b) Chandrasekhar, V.; Sasikumar, P.; Thilagar, P. Organometallics 2007, 26, 4386.
  • (a) Anderton, M. J.; Manson, M. M.; Verschoyle, R.; Gescher, A.; Steward, W. P.; Williams, M. L.; Mager, D. E. Drug Metab. Dispos. 2004, 32, 632; (b) Bonnesen, C.; Eggleston, I. M.; Hayes, J. D. Cancer Res. 2001, 61, 6120; (c) Chang, Y. C.; Riby, J.; Chang, G. H.; Peng, B.; Firestone, G. L.; Bjeldanes, L. F. Biochem. Pharmacol. 1999, 58, 825; (d) Le, H. T.; Schaldach, C. M.; Firestone, G. L.; Bjeldanes, L. F. J. Biol. Chem. 2003, 278, 21136; (e) Hong, C.; Firestone, G. L.; Bjeldanes, L. F. Biochem. Pharmacol. 2002, 63, 1085.
  • (a) Deb, M. L.; Baruah; B.; Bhuyan, P. J. Synthesis 2008, 286; (b) Deb, M. L.; Bhuyan, P. J. Synlett 2008, 325.
  • (a) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250; (b) Pu, F.; Li, Y.; Song, Y.-H.; Xiao, J.; Liu, Z.-W.; Wang, C.; Liu, Z.-T.; Chen, J.-G.; Lu, J. Adv. Synth. Catal. 2016, 358, 539; (c) Li, X. L.; Wang, Y. M.; Tian, B.; Matsuura, T.; Meng, J. B. J. Heterocycl. Chem. 1998, 35, 129; (d) Azizian, J.; Mohammadizadeh, M. R.; Teimouri, F.; Mohammadi, A. A.; Karimi, A. R. Synth. Commun. 2006, 36, 3631; (e) Kidwai, M.; Bansal, V.; Mothsra, P.; Saxena, S.; Somvanshi, R. K.; Dey, S.; Singh, T. P. J. Mol. Cat. A: Chem. 2007, 268, 76; (f) Hagiwara, H.; Fujimoto, N.; Suzuki, T.; Ando, M. Heterocycles 2000, 53, 549.
  • (a) Betti, M. Gazz. Chim. Ital. 1900, 30, 301; (b) Deb, M. L.; Dey, S. S.; Bento, I.; Barros, M. T.; Maycock, C. D. Angew. Chem. Int. Ed. 2013, 52, 9791; (c) Deb, M. L.; Pegu, C. D.; Borpatra, P. J.; Baruah, P. K. RSC Adv. 2016, 6, 40552.
  • (a) Xiong, S.; Steelman, D. K.; Medvedev, G. A.; Delgass, W. N.; Abu-Omar, M. M.; Caruthers, J. M. ACS Catal. 2014, 4, 1162; (b) Wang, T.-W.; Intaranukulkit, T.; Rosana, M. R.; Slegeris, R.; Simon, J.; Dudley, G. B. Org. Biomol. Chem. 2012, 10, 248; (c) Finneman, J. I.; Fishbein, J. C. J. Am. Chem. Soc. 1995, 117, 4228; (d) Fountain, K. R.; Tad-y, D. B.; Paul, T. W.; Golynskiy, M. V. J. Org. Chem. 1999, 64, 6547.
  • Deb, M. L.; Pegu, C. D.; Deka, B.; Dutta, P.; Kotmale, A. S.; Baruah, P. K. Eur. J. Org. Chem. 2016, 3441.
  • For reviews on microwave-assisted organic synthesis, see (a) Moseley, J. D.; Kappe, C. O. Green Chem. 2011, 13, 794; (b) Microwaves in Organic Synthesis; Loupy, A. (Ed.); Wiley-VCH: Weinheim, Germany, 2006); (c) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250; (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
  • (a) Modi, A.; Ali, W.; Patel, B. K. Adv. Synth. Catal. 2016, 358, 2100; (b) Kaswan, P.; Nandwana, N. K.; DeBoef, B.; Kumar, A. Adv. Synth. Catal. 2016, 358, 2108; (c) Pu, F.; Li, Y.; Song, Y.-H.; Xiao, J.; Liu, Z.-W.; Wang, C.; Liu, Z.-T.; Chen, J.-G.; Lu, J. Adv. Synth. Catal. 2016, 358, 539.
  • (a) Wilcke, D.; Herdtweck, E.; Bach, T. Synlett 2011, 1235; (b) Zhao, W.; Wang, Z.; Chu, B.; Sun, J. Angew. Chem. Int. Ed. 2015, 54, 1910; (c) Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733.

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