Journal of the American Chemical Society
Communication
(13) Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129,
6098.
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and analytical data for new com-
pounds and products. This material is available free of charge
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S
(14) Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255. For
comparison, bond dissociation enthalpies ΔH298 (in kcal/mol) = Ph−
H, 113; Ph−OMe, 101; Ph−NH2, 104; vs Ph-Br, 84.
(15) Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem.
Soc. 2006, 128, 16516.
(16) For impact of DoM and DreM strategies, see: (a) Snieckus, V.;
Macklin, T. In Handbook of C−H Transformations; Dyker, G., Ed.;
Wiley: Weinheim, 2005; Vol. 1, p 106. (b) Hartung, C. G.; Snieckus,
V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley: Weinheim, 2002;
p 330. (c) Snieckus, V. Chem. Rev. 1990, 90, 879. (d) Whisler, M. C.;
MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43,
2206. For impact of DoM/cross-coupling strategy, see: (e) Snieckus,
V.; Anctil, E. J. G. In Metal-Catalyzed Cross-Coupling Reactions and
More; de Meijere, A., Brase, S., Oestreich, M., Eds.; Wiley: Weinheim,
2014; Vol. 3, p 1067 (f) Board, J.; Cosman, J. L.; Rantanen, T.; Singh,
S. P.; Snieckus, V. Platinum Metals Rev. 2013, 57, 234. (g) Anctil, E. J.
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AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful to Dr. Francoise Sauriol (Queen’s University)
for assistance in NMR spectroscopy, Dr. Jiaxi Wang (Queen’s
University) for discussion of MS spectra, and NSERC Canada
(Discovery Grant) for continuing support of our synthetic
programs.
(17) For amide-to-aldehyde conversion using the Schwartz reagent,
see: (a) Zhao, Y.; Snieckus, V. Org. Lett. 2014, 16, 390−393. (b) Zhao,
Y.; Snieckus, V. U.S. Patent 8,168,833, 2012.
For other
transfomations of amides, see: (c) Larock, R. C. Comprehensive
Organic Transformations. A Guide to Functional Group Preparations, 2nd
ed.; Wiley: New York, 2010.
(18) To the best of our knowledge, two cases of tertiary amide-
mediated C−H activation/aryl−aryl coupling reactions have been
reported; however, the amide-mediated C−O activation/coupling
reaction is still unknown. (a) Wencel-Delord, J.; Nimphius, C.; Wang,
H. G.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 13001. (b) Okazawa,
T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124,
5286.
(19) Kaye, G. W. C.; Laby, T. H. Tables of Physical and Chemical
Constants, 16th ed.; Longman: New York, 1995.
(20) (a) Beak, P.; Brown, R. A. J. Org. Chem. 1982, 47, 34. (b) Ludt,
R. E.; Griffiths, J. S.; McGrath, K. N.; Hauser, C. R. J. Org. Chem. 1973,
38, 1668.
REFERENCES
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