Organic Letters
Letter
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photocatalyst. The above-mentioned results suggested the rate
of this reaction was related to the concentration of aldehyde
and photocatalyst.
In conclusion, we have developed a simple and general
method for the acetalization of aldehydes by means of a
photochemical reaction with Eosin Y as the photocatalyst. A
variety of dimethyl acetals and cyclic acetals can be achieved in
good yields under neutral conditions. The challenging acid-
sensitive aldehydes and sterically hindered aldehydes are also
well-tolerated. This system exhibits chemoselectivity for the
aldehydes. Mechanistic insights indicate that visible light plays a
vital role in this transformation. The detailed mechanism is
currently under investigation in our laboratory and will be
reported in the near future.
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(b) Hopkinson, M. N.; Sahoo, B.; Li, J. L.; Glorius, F. Chem. - Eur. J.
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ASSOCIATED CONTENT
* Supporting Information
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S
(5) (a) Cherevatskaya, M.; Neumann, M.; Fuldner, S.; Harlander, C.;
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The Supporting Information is available free of charge on the
Kummel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; Konig, B. Angew.
̈
̈
Chem., Int. Ed. 2012, 51, 4062. (b) Fidaly, K.; Ceballos, C.; Falguieres,
A.; Veitia, M. S.-I.; Guy, A.; Ferroud, C. Green Chem. 2012, 14, 1293.
(c) Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc.
The experimental procedure, characterization data, and
1
copies of H and 13C NMR spectra (PDF)
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2009, 131, 10875. (d) Neumann, M.; Fuldner, S.; Konig, B.; Zeitler, K.
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Angew. Chem., Int. Ed. 2011, 50, 951. (e) Neumann, M.; Zeitler, K.
Org. Lett. 2012, 14, 2658. (f) Nicewicz, D. A.; MacMillan, D. W.
Science 2008, 322, 77. (g) Pirnot, M. T.; Rankic, D. A.; Martin, D. B.;
MacMillan, D. W. Science 2013, 339, 1593. (h) Shih, H.-W.; Vander
Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc.
2010, 132, 13600. (i) Yoon, H.-S.; Ho, X.-H.; Jang, J.; Lee, H.-J.; Kim,
S.-J.; Jang, H.-Y. Org. Lett. 2012, 14, 3272.
AUTHOR INFORMATION
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Corresponding Author
ORCID
(6) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
(7) (a) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
(b) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107,
5606.
Author Contributions
§H.Y. and L.N. contributed equally.
(8) (a) de Lijser, H. J. P.; Rangel, N. A. J. Org. Chem. 2004, 69, 8315.
(b) de Lijser, H. J. P.; Tsai, C.-K. J. Org. Chem. 2004, 69, 3057.
(9) Oates, R. P.; Jones, P. B. J. Org. Chem. 2008, 73, 4743.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by the 973 Program (2011CB808600,
2012CB725302, 2013CB834804), the National Natural Science
Foundation of China (21390400, 21272180, 21302148,
2109343, and 21402217), the Research Fund for the Doctoral
Program of Higher Education of China (20120141130002), the
Ministry of Science and Technology of China
(2012YQ120060), and the Program for Changjiang Scholars
and Innovative Research Team in University (IRT1030). The
Program of Introducing Talents of Discipline to Universities of
China (111 Program) is also appreciated. We thank Prof. Ang
Li at Shanghai Institute of Organic Chemistry for providing the
chemical materials.
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