Ammonium Chloride/B(C6F5)3 System Catalyzed Selective Addition of Acids to Alkynes
- Corresponding author: Nie Wanli, niewl126@126.com
Citation: Wen Zhiguo, Tian Chong, Borzov Maxim V., Nie Wanli. Ammonium Chloride/B(C6F5)3 System Catalyzed Selective Addition of Acids to Alkynes[J]. Acta Chimica Sinica, ;2016, 74(6): 498-502. doi: 10.6023/A16040164
Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew Chem., Int. Ed. 2007, 119, 8196. (b) Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Froehlich, R.; Erker, G. Angew Chem., Int. Ed., 2008, 120, 7654. (c) Wang, H.; Foehlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2008, 5966.
Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew Chem., Int. Ed. 2007, 119, 8196. (b) Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Froehlich, R.; Erker, G. Angew Chem., Int. Ed., 2008, 120, 7654. (c) Wang, H.; Foehlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2008, 5966.
Chen, C.; Eweiner, F.; Wibbeling, B.; Fröhlich, R.; Senda, S.; Ohki, Y.; Tatsumi, K.; Grimme, S.; Kehr, G.; Erker, G. Chem. Asian J. 2010, 5, 2199. (b) Liedtke, R.; Fröhlich, R.; Kehr, G.; Erker, G. Organometallics 2011, 30, 5222. (c) Dierker, G.; Ugolotti, J.; Kehr, G.; Fröhlich, R.; Erker, G. Adv. Synth. Catal. 2009, 351, 1080.
Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396. (b) Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6594. (c) Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6422.
Chen, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2010, 132, 13594. (b) Chen, C.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2010, 46, 3580. (c) Chen, C.; Voss, T.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett. 2011, 13, 62. (d) Ekkert, O.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2011, 133, 4610. (e) Kehr, G.; Erker, G. Chem. Commun. 2012, 48, 1839. (f) Jiang, C. F.; Blacque, O.; Berke, H. Organometallics 2010, 29, 125.
Chernichenko, k.; Madarasz, A.; Papai, I.; Nieger, M.; Leskelae, M.; Repo, T. Nat. Chem. 2013, 5, 718.
Mahdi, T.; Stephan, D. W. J. Am. Chem. Soc. 2014, 136, 15809. (b) Scott, D. J.; Fuchter, M. J.; Ashley, A. E. J. Am. Chem. Soc. 2014, 136, 15813.
Griesbaum, K.; Rao, R.; Leifker, G. J. Org. Chem. 1982, 47, 4975. (b) Kropp, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102. (c) Klein, H.; Roisnel, T.; Brunean, C.; Derien, S. Chem. Commun. 2012, 48, 11032. (d) Derien, S.; Klein, H.; Brunean, C. Angew. Chem., Int. Ed. 2015, 54, 12112.
Michal, R.; Youval, S. Organometallics 1983, 2, 1689. (b) Muriel, N.; Benedicte, S.; Frauke, H.; Brunean, C.; Dixneuf, P. H. J. Organomet. Chem. 1993, 451, 133. (c) Muriel, N.; Christian, B.; Serge, L.; Dixneuf, P. H. Tetrahedron 1993, 49(13), 2629. (d) Olivier, L.; Pierre, H. D. J. Organomet. Chem. 1995, 488, C9. (e) Lukas, J. G.; Jens, P.; Debasis, K. Chem. Commun. 2003, 706. (f) Victorio, C.; Javier, F.; Jose, G. Organometallics 2011, 30, 852. (g) Jena, R. K.; Bhattacgarjee, M. Eur. J. Org. Chem. 2015, 6734.
Recently we have studied the reactivity of different kind of ammonium halide/BCF systems in respect to alkynes, and have found that the stability of a suspected σ-adduct seems to be dependent upon the nature of both the halide anion and ammonium counterion (quaternary or else). Unfortunately, the expected intermediates could not been trustworthily observed by NMR spectroscopy. This part of work is still in progress.
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