Organic Letters
Letter
(10) Abrams, M. L.; Buser, J. Y.; Calvin, J. R.; Johnson, M. D.; Jones,
B. R.; Lambertus, G.; Landis, C. R.; Martinelli, J. R.; May, S. A.;
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the ease of the reaction setup, the mildness of the reaction
conditions, and the commercial availability of all reagents
suggest that this method could find valuable application with
compatible substrates.
ASSOCIATED CONTENT
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S
* Supporting Information
The Supporting Information is available free of charge on the
Experimental procedures and characterization data for all
(13) Hoover, J. M.; Ryland, B. L.; Stahl, S. S. ACS Catal. 2013, 3,
2599.
(14) For TEMPO/NOx-catalyzed methods, see: (a) Liu, R.; Liang,
X.; Dong, C.; Hu, X. J. Am. Chem. Soc. 2004, 126, 4112. (b) Liu, R.;
Dong, C.; Liang, X.; Wang, X.; Hu, X. J. Org. Chem. 2005, 70, 729.
(c) Xie, Y.; Mo, W.; Xu, D.; Shen, Z.; Sun, N.; Hu, B.; Hu, X. J. Org.
Chem. 2007, 72, 4288. (d) Wang, X.; Liu, R.; Jin, Y.; Liang, X. Chem. -
Eur. J. 2008, 14, 2679. (e) Tao, J.; Lu, Q.; Chu, C.; Liu, R.; Liang, X.
Synthesis 2010, 2010, 3974. (f) He, X.; Shen, Z.; Mo, W.; Sun, N.; Hu,
B.; Hu, X. Adv. Synth. Catal. 2009, 351, 89. (g) Miao, C.-X.; He, L.-N.;
Wang, J.-L.; Wu, F. J. Org. Chem. 2010, 75, 257.
AUTHOR INFORMATION
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Corresponding Authors
Notes
The authors declare no competing financial interest.
(15) For bicyclic-nitroxyl/NOx-catalyzed methods, see: (a) Kuang,
Y.; Rokubuichi, H.; Nabae, Y.; Hayakawa, T.; Kakimoto, M.-A. Adv.
Synth. Catal. 2010, 352, 2635. (b) Shibuya, M.; Osada, Y.; Sasano, Y.;
Tomizawa, M.; Iwabuchi, Y. J. Am. Chem. Soc. 2011, 133, 6497.
(c) Lauber, M. B.; Stahl, S. S. ACS Catal. 2013, 3, 2612.
(16) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem.
1987, 52, 2559.
(17) For other non-aerobic conditions that warrant consideration, see
ref 4. Pinnick conditions have been applied successfuly to a related
substrates. See ref 10 and the following: Krishna, P. R.; Arun Kumar, P.
V.; Mallula, V. S.; Ramakrishna, K. V. S. Tetrahedron 2013, 69, 2319.
(18) For context, see: Marteau, C.; Ruyffelaere, F.; Aubry, J.-M.;
Penverne, C.; Favier, D.; Nardello-Rataj, V. Tetrahedron 2013, 69,
2268.
ACKNOWLEDGMENTS
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We are grateful to a consortium of pharmaceutical companies
(Eli Lilly, Pfizer, and Merck), the NIH (R01-GM100143 to
SSS) and the National Science Foundation (CHE-1152989 to
CRL) for financial support of this work. NMR spectroscopy
facilities were supported in part by the NSF (CHE-1048642).
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