Journal of the American Chemical Society
Article
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(7) We recently reported a chemo- and regioselective aerobic
oxidation of phenols to ortho-quinones: Esguerra, K. V. N.; Fall, Y.;
Lumb, J.-P. Angew. Chem., Int. Ed. 2014, DOI: 10.1002/
anie.201311103.
provides an exceptionally efficient means of producing
molecular complexity. Our work takes an important step
toward the development of general catalytic aerobic conditions
that should facilitate future mechanistic investigations and
synthetic applications.
ASSOCIATED CONTENT
* Supporting Information
■
S
Synthetic procedures, characterization and additional data. This
material is available free of charge via the Internet at http://
(8) Ling, K.-Q.; Lee, Y.; Macikenas, D.; Protasiewicz, J. D.; Sayre, L.
M. J. Org. Chem. 2003, 68, 1358−1366.
AUTHOR INFORMATION
Corresponding Author
■
(9) For general reviews on the oxidative dearomatization of phenols
and its use in synthesis, see: (a) Pouyseg
S. Tetrahedron 2010, 66, 2235−2261. (b) Quideau, S.; Deffieux, D.;
Douat-Casassus, C.; Pouysegu, L. Angew. Chem., Int. Ed. 2011, 50,
́
u, L.; Deffieux, D.; Quideau,
Notes
́
586−621. (c) Roche, S. P.; Porco, J. A. Angew. Chem., Int. Ed. 2011, 50,
4068−4093. For the stoichiometric oxidation of phenols to ortho-
quinones, see: (d) Magdziak, D.; Rodriguez, A. A.; Van De Water, R.
W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285−288 (and references
therein). (e) Uyanik, M.; Mutsuga, T.; Ishihara, K. Molecules 2012, 17,
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Tuczek, F. Chem. Soc. Rev. 2011, 40, 4077−4098.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank Professor Barry M. Trost for insightful discussions,
along with Professors Xavier Ottenwaelder (Concordia
University), Allan Hay (McGill University), James Gleason
(McGill University), and Bruce Arndtsen (McGill University).
Financial support was provided by the Natural Sciences and
Engineering Council of Canada (Discovery Grant to J.-P.L.),
(11) (a) Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev.
2004, 104, 1013−1045. (b) Lewis, E. A.; Tolman, W. B. Chem. Rev.
2004, 104, 1047−1076.
́
the Fonds de Recherche du Quebec - Nature et Technologies
(Team Grant to J.P.L.), McGill University-Canadian Institutes
of Health Drug Development Trainee Program (doctoral
fellowship to K.V.N.E.), and McGill University (start-up funds
to J.P.L.).
(12) Hoffmann, A.; Citek, C.; Binder, S.; Goos, A.; Rubhausen, M.;
̈
́ ́
Troeppner, O.; Ivanovic-Burmazovic, I.; Wasinger, E. C.; Stack, T. D.
P.; Herres-Pawlis, S. Angew. Chem., Int. Ed. 2013, 52, 5398−5401.
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Commun. 1990, 1752−1755. (b) Casella, L.; Gullotti, M.; Radaelli, R.;
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(c) Osako, T.; Ohkubo, K.; Taki, M.; Tachi, Y.; Fukuzumi, S.; Itoh, S.
J. Am. Chem. Soc. 2003, 125, 11027−11033. (d) Rolff, M.;
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49, 6438−6442. (e) Hamann, J. N.; Tuczek, F. Chem. Commun. 2014,
50, 2298−2300.
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