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Al-Saedy, M.A.E.; Harrity, J.P.A. (2016)
Publisher: Georg Thieme Verlag
Languages: English
Types: Article
Subjects:
We report herein that 3-pinacol boronic esters undergo facile protodeborylation in the presence of palladium catalysts and base, and this contributes significantly to the generation of nonborylated indole byproducts in the B2Pin2-mediated palladium-catalysed borylative cyclization of 2-alkynylanilides. Suginome’s reagent provides an alternative method to access 3-borylated indoles as these compounds are less susceptible to protodeborylation.
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    • (1) Boronic Acids, Ed: D.G. Hall, WILEY-VCH, Weinheim, 2005.
    • (2) For representative examples see: (a) Bachollet, S. P. J. T.; Vivat, J. F.; Cocker, D. C.; Adams, H.; Harrity, J. P. A. Chem. Eur. J., 2014, 20, 12889; (b) Crépin, D. F. P.; Harrity, J. P. A.; Jiang, J.; Meijer, A. J. H. M.; Nassoy, A.-C. M. A.; Raubo, P. J. Am. Chem. Soc. 2014, 136, 8642; (c) Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. J. Org. Chem. 2009, 74, 396; (d) Delaney, P. M.; Browne, D. L.; Adams, H.; Plant, A.; Harrity, J. P. A. Tetrahedron 2008, 64, 866.
    • (3) (a) Stalling, T.; Harker, W. R. R.; Auvinet, A.-L.; Cornel, E. J.; Harrity, J. P. A. Chem. Eur. J. 2015, 21, 2710; (b) Auvinet, A.-L.; Harrity, J. P. A. Angew. Chem. Int. Ed. 2011, 50, 2769; (c) Auvinet, A.-L.; Harrity, J. P. A.; Hilt, G. J. Org. Chem. 2010, 75, 3893; (d) Gandon, V.; Leboeuf, D.; Amslinger, S.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Angew. Chem. Int. Ed. 2005, 44, 7114; e) Hilt, G.; Smolko, K. I. Angew. Chem. Int. Ed. 2003, 42, 2795.
    • (4) Kirkham, J. D.; Edeson, S. J.; Stokes, S.; Harrity, J. P. A. Org. Lett. 2012, 14, 5354.
    • (5) a) Huang, J.; Macdonald, S. J. F.; Harrity, J. P. A. Chem. Commun. 2010, 46, 8770; b) Warner, A. J.; Lawson, J. R.; Fasano, V.; Ingleson, M. J. Angew. Chem. Int. Ed. 2015, 54, 11245; c) Chong, E.; Blum, S. A. J. Am. Chem. Soc. 2015, 137, 10144.
    • (6) For alternative approaches to 3-borylated indoles see: (a) Tasch, B. O. A.; Merkul, E.; Müller, T. J. J. Eur. J. Org. Chem. 2011, 4532; (b) Merkul, E.; Schäfer, E.; Müller, T. J. J. Org. Biomol. Chem. 2011, 9, 3139; (c) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B., Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
    • (7) Cacchi, S.; Fabrizi G. Chem. Rev. 2005, 105, 2873.
    • (8) Iwadate, N.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 2548.
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