Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 10
438
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

p-Toluenesulfonic acid-promoted autocatalytic hydrolyzation of 1-tosyl-1,2,3-triazoles

, , , , , , & show all
Pages 1227-1234 | Received 03 Dec 2017, Published online: 02 Apr 2018

References

  • (a) Gánti, T. The Principles of Life; Oxford University Pres: Oxford, 2003; (b) Luisi, P. L. The Emergence of Life; Cambridge University Press: Cambridge, UK, 2006; (c) Ruiz-Mirazo, K.; Briones, C.; de la Escosura, A. Chem. Rev. 2014, 114, 285.
  • (a) Blackmond, D. G. Angew. Chem. Int. Ed. 2009, 48, 386; (b) Dadon, Z.; Wagner, N.; Ashkenasy, G. Angew. Chem. Int. Ed. 2008, 47, 6128.
  • (a) Bissette, A. J.; Fletcher, S. P. Angew. Chem. Int. Ed. 2013, 52, 12800; (b) Tsogoeva, S. B. J. Syst. Chem. 2010, 1, 8.
  • (a) Inoue, T.; Orgel, L. E. Science 1983, 219, 859; (b) Engelhart, A. E.; Powner, M. W.; Szostak, J. W. Nat. Chem. 2013, 5, 390.
  • (a) Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadiri, M. R. Nature 1996, 382, 525; (b) Yao, S.; Ghosh, I.; Zutshi, R.; Chmielewski, J. Nature 1998, 396, 447; (c) Carnall, J. M. A.; Waudby, C. A.; Belenguer, A. M.; Stuart, M. C. A.; Peyralans, J. J.-P.; Otto, S. Science 2010, 327, 1502.
  • Klussmann, M.; Iwamura, H.; Mathew, S. P.; Wells Jr, D. H.; Pandya, U.; Armstrong, A.; Blackmond, D. G. Nature 2006, 441, 621.
  • (a) Singh, K. J.; Hoepker, A. C.; Collum, D. B. J. Am. Chem. Soc. 2008, 130, 18008; (b) Ma, Y.; Hoepker, A. C.; Gupta, L.; Faggin, M. F.; Collum, D. B. J. Am. Chem. Soc. 2010, 132, 15610; (c) Hoepker, A. C.; Gupta, L.; Ma, Y.; Faggin, M. F.; Collum, D. B. J. Am. Chem. Soc. 2011, 133, 7135.
  • (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382; (b) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767.
  • (a) Kondepudi, D. K.; Asakura, K. Acc. Chem. Res. 2001, 34, 946; (b) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369; (c) Flegeau, E. F.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. J. Am. Chem. Soc. 2011, 133, 10161; (d) Rao, C. N.; Hoz, S. J. Am. Chem. Soc. 2011, 133, 14795; (e) Giri, R.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 15860; (f) Mauksch, M.; Tsogoeva, S. B.; Martynova, I. M.; Wei, S. Angew. Chem. Int. Ed. 2007, 46, 393.
  • Yun, Y.; Gellman, A. J. Nat. Chem. 2015, 7, 520.
  • Bordwell, F. G.; Algrim, D. J. Org. Chem. 1976, 41, 2507.
  • Akiyama, T.; Mori, K. Chem. Rev. 2015, 115, 9277.
  • Namba, K.; Osawa, A.; Ishizaka, S.; Kitamura, N.; Tanino, K. J. Am. Chem. Soc. 2011, 133, 11466.
  • Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
  • (a) Chattopadhyay, B.; Gevorgyan, V. Angew. Chem. Int. Ed. 2012, 51, 862; (b) Gulevich, A. V.; Gevorgyan, V. Angew. Chem. Int. Ed. 2013, 52, 1371; (c) Davies, H. M. L.; Alford, J. S. Chem. Soc. Rev. 2014, 43, 5151.
  • (a) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905; (b) Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249; (c) Tron, G. C.; Pirali, T.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278; (d) Agalave, S. G.; Maujan, S. R.; Pore, V. S. Chem. Asian J. 2011, 6, 2696.
  • (a) Chu, C.-H.; Liu, R.-H. Chem. Soc. Rev. 2011, 40, 2177; (b) Lau, Y. H.; Rutledge, P. J.; Watkinson, M. Chem. Soc. Rev. 2011, 40, 2848; (c) Astruc, D.; Liang, L.-Y.; Ruiz, J. Acc. Chem. Res. 2012, 45, 630; (d) Muller, T.; Brase, S. Angew. Chem. 2011, 123, 12046 (e) Muller, T.; Brase, S. Angew. Chem. Int. Ed. 2011, 50, 11844.
  • (a) Chattopadhyay, B.; Gevorgyan, V. Angew. Chem. 2012, 124, 886; (b) Miura, T.; Yamauchi, M.; Murakami, M. Chem. Commun. 2009, 1470; (c) Chattopadhyay, B.; Gevorgyan, V. Org. Lett. 2011, 13, 3746; (d) Horneff, T.; Chuprakov, S.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972; (e) Miura, T.; Fujimoto, Y.; Murakami, M. Angew. Chem. Int. Ed. 2015, 54, 9967; (f) Miura, T.; Fujimoto, Y.; Murakami, M. Angew. Chem. 2015, 127, 10105; (g) Zibinsky, M.; Fokin, V. V. Angew. Chem. Int. Ed. 2013, 52, 1507; (h) Zibinsky, M.; Fokin, V. V. Angew. Chem. 2013, 125, 1547; (i) Grimster, N.; Zhang, L.; Fokin, V. V. J. Am. Chem. Soc. 2010, 132, 2510; (j) Kwok, S. W.; Zhang, L.; Fokin, V. V. Angew. Chem. Int. Ed. 2014, 53, 3452; (k) Kwok, S. W.; Zhang, L.; Fokin, V. V. Angew. Chem. 2014, 126, 3520; (l) Urankar, D.; Pinter, B.; Kosmrlj, J. Inorg. Chem. 2010, 49, 4820; (m) Johnson, T. C.; Totty, W. G.; Wills, M. Org. Lett. 2012, 14, 5230; (n) Saleem, F.; Rao, G. K.; Singh, A. K. Organometallics 2013, 32, 3595.
  • (a) Ueda, S.; Su, M.-J.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50, 8944; (b) Ueda, S.; Su, M.-J.; Buchwald, S. L. Angew. Chem. 2011, 123, 9106; (c) Wang, X.-J.; Zhang, L.; Senanayake, C. H. Org. Lett. 2009, 11, 5026; (d) Liu, Y.-X.; Yan, W.-M.; Shi, X.-D. Org. Lett. 2008, 10, 5389; (e) Chen, Y.-F.; Liu, Y.-X.; Shi, X.-D. Chem. Commun. 2008, 3254; (f) Xu, K.; Thieme, N.; Breit, B. Angew. Chem. Int. Ed. 2014, 53, 7268; (g) Xu, K.; Thieme, N.; Breit, B. Angew. Chem. 2014, 126, 7396.
  • (a) Duan, H.-F.; Sengupta, S.; Shi, X.-D. J. Am. Chem. Soc. 2009, 131, 12100; (b) Duan, H.-F.; Sengupta, S.; Shi, X.-D. Organometallics 2009, 28, 2352.
  • (a) Hu, L.; Wang, T.; He, G.-F. Chem. Eur. J. 2016, 22, 911; (b) Hu, Q.-Q.; Li, Y.-J.; Chen, Y.-F. Adv. Synth. Catal. 2016, 358, 1689; (c) Journet, M.; Cai, D.-W.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117; (d) Li, J.-H.; Wang, D.; Chen, B.-H. Org. Lett. 2009, 11, 3024; (e) Sengupta, S.; Duan, H.-F.; Shi, X.-D. Org. Lett. 2008, 10, 1493; (f) Ponpandian, T.; Muthusubramanian, S. Tetrahedron Lett. 2012, 53, 59; (g) Quan, X.-J.; Ren, Z.-H.; Guan, Z.-H.; Org. Lett. 2014, 16, 5728; (h) Amantini, D.; Fringuelli, F.; Vaccaro, L. J. Org. Chem. 2005, 70, 6526; (i) Barluenga, J.; Valdes, C.; Beltran, G. Angew. Chem. Int. Ed. 2006, 45, 6893; (j) Tsai, C. W.; Yang, S. C.; Wu, M. J. Tetrahedron 2009, 65, 8367.
  • (a) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786; (b) Kamijo, S.; Huo, Z. B.; Yamamoto, Y. J. Org. Chem. 2005, 70, 6389; (c) Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171; (d) Cohrt, A. E.; Jensen, J. F.; Nielsen, T. E. Org. Lett. 2010, 12, 5414.
  • Motoshi, Y.; Tomoya, M.; Masahiro, M. Heterocycles 2010, 80, 177.
  • Tsogoeva, S. B. J. Sys. Chem. 2010, 1, 8.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.