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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 19
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Original Articles

B(C6F5)3-catalyzed synthesis of benzylic azides

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Pages 1771-1776 | Received 27 Jun 2017, Published online: 31 Aug 2017

References

  • Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed. 2005, 44, 5188.
  • For representative examples, see: (a) Benati, L.; Bencivenni, G.; Leardini, R.; Nanni, D.; Minozzi, M.; Spagnolo, P.; Scialpi, R.; Zanardi, G. Org. Lett. 2006, 8, 2499; (b) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906; (c) Postigo, A.; Kopsov, S.; Ferreri, C.; Chatgilialoglu, C. Org. Lett. 2007, 9, 5159.
  • For a review, see: Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302; See also: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596; (b) Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210; (c) Worell, B. T.; Malik, J. A.; Fokin, V. V. Science, 2013, 340, 457.
  • (a) Yang, M.; Li, J.; Chen, P. R. Chem. Soc. Rev. 2014, 43, 6511; (b) Li, L.; Zhang, Z. Molecules 2016, 21, 1393; (c) Sletten, E. M.; Bertozzi, C. R. Acc. Chem. Res. 2011, 44, 666; (d) Pasini, D. Molecules 2013, 18, 9512; (e) Nwe, K.; Brechbiel, M. W. Cancer Biother Radiopharm 2009, 24, 289.
  • Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
  • Mitsunobu type conversion of alcohol to azide: (a) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100; (b) Viaud, M. C.; Rollin, P. Synthesis 1990, 130; (c) Saito, A.; Saito, K.; Tanaka, A.; Oritani, T. Tetrahedron Lett. 1997, 38, 3955.
  • (a) Kim, S.; Chung, K. N.; Ynag, S. J. Org. Chem. 1987, 52, 3917; (b) Sharma, G. V. M.; Kumar, K. R.; Sreenivas, P.; Krishna, P. R.; Chorghade, M. S. Tetrahedron: Asymmetry 2002, 13, 687; (c) Kim, S. H.; Shin, C.; Pai, A. N.; Koh, H. K.; Chang, M. H.; Chung, B. Y.; Cho, Y. S. Synthesis 2004, 1581; (d) Terrassson, V.; Marque, S.; Georgy, M.; Campagne, J.-M.; Prim, D. Adv. Synth. Catal. 2006, 348, 2063.
  • (a) Chan, L. Y.; Kim, S.; Chung, W. T.; Long, C.; Kim, S. Synlett 2011, 415; (b) Sawama, Y.; Nagata, S.; Yabe, Y.; Morita, K.; Monguchi, Y.; Sajiki, H.; Chem. Eur. J. 2012, 18, 16608; (c) Sawama, Y.; Goto, R.; Nagata, S.; Shishido, Y.; Monguchi, Y.; Sajiki, H. Chem. Eur. J. 2014, 20, 2631.
  • (a) Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S.; Thongaram, P.; Kaewmee, B. Synthesis 2015, 47, 323; (b) Sawama, Y.; Nagata, S.; Yabe, Y.; Morita, K.; Monguchi, Y.; Sajiki, H. Chem. Eur. J. 2012, 18, 16608.
  • For reviews of B(C6F5)3, see: (a) Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345; (b) Piers, W. E. Adv. Organomet. Chem. 2004, 52, 1; (c) Erker, G. Dalton Trans. 2005, 1883; (d) Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124; (e) Stephan, D. W.; Erker, G. Angew. Chem. Int. Ed. 2010, 49, 46; (f) Piers, W. E.; Marwitz, A. J. V.; Mercier, L. G. Inorg. Chem. 2011, 50, 12252; (g) Melen, R. L. Chem. Commun. 2014, 50, 1161; (h) Lawson, J. R.; Melen, R. L. Inorg. Chem. 2017, doi:10.1021/acs.inorgchem.6b02911.
  • (a) Gevorgyan, V.; Liu, J.-X.; Rubin, M.; Benson, S.; Yamamoto, Y. Tetrahedron Lett. 1990, 1990, 40, 8919; (b) Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179; (c) Gevorgyan, V.; Rubin, M.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2001, 66, 1672; (d) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090.
  • Rubin, M.; Schwier, T.; Gevorgyan, V. J. Org. Chem. 2002, 67, 1936.
  • (a) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705; (b) Schwier, T.; Rubin, M.; Gevorgyan, V. Org. Lett. 2004, 6, 1999.
  • Focante, F.; Mercandelli, P.; Sironi, A.; Resconi, L. Coord. Chem. Rev. 2006, 250, 170.
  • Fraenk, W.; Klapötke, T. M.; Krumm, B.; Nöth, H.; Suter, M.; Vogt, M.; Warchhold, M. Can. J. Chem. 2002, 80, 1444.
  • (a) Horton, A. D.; de With, J. Organometallics 1997, 16, 5424; (b) Köhler, K.; Piers, W. E.; Xin, S.; Feng, Y.; Bravakis, A. M.; Jarvis, A. P.; Collins, S.; Clegg, W.; Yap G. P. A.; Marder, T. B. Organometallics 1998, 17, 3557; (c) Williams, V. C.; Dai, C.; Li, Z.; Collins, S.; Piers, W. E.; Clegg, W. C.; Elsegood, M. R. J.; Marder, T. B. Angew. Chem., Int. Ed. 1999, 38, 3695; (d) Köhler, K.; Piers, W. E. Can. J. Chem. 1998, 76, 1249.
  • Bigler, R.; Huber, R.; Mezzetti, A. Angew. Chem. Int. Ed. 2015, 54, 5171.
  • Kobayashi, M.; Okamoto, S. Tetrahedron Lett. 2006, 47, 4347.
  • Khedar, P.; Pericherla, K.; Kumar, A. Synlett 2014, 25, 515.

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