Organic Letters
Letter
Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317−5325. (k) Zheng,
Q.-H.; Meng, W.; Jiang, G.-J.; Yu, Z.-X. Org. Lett. 2013, 15, 5928−5931.
(l) Min, C.; Sanchawala, A.; Seidel, D. Org. Lett. 2014, 16, 2756−2759.
(5) For ruthenium catalysis: (a) Murahashi, S.-I.; Komiya, N.; Terai,
H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312−15313.
(b) Murahashi, S.-I.; Komiya, N.; Terai, H. Angew. Chem., Int. Ed.
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(c) Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem.
radical-mediated processes, and to apply it in directed SAR
studies.13,14
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
́ ́
Soc. 2008, 130, 11005−11012. (d) Condie, A. G.; Gonzalez-Gomez, J.
Experimental details, spectral data, and copies of NMR
spectra for all new compounds (PDF)
C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464−1465.
(e) Barham, J. P.; John, M. P.; Murphy, J. A. Beilstein J. Org. Chem. 2014,
10, 2981−2988. (f) Bergonzini, G.; Schindler, C. S.; Wallentin, C.-J.;
Jacobsen, E. N.; Stephenson, C. R. J. Chem. Sci. 2014, 5, 112−116.
(6) For iron catalysis: (a) Bi, H.-P.; Chen, W.-W.; Liang, Y.-M.; Li, C.-J.
Org. Lett. 2009, 11, 3246−3249. (b) Volla, M. R.; Vogel, P. Org. Lett.
2009, 11, 1701−1704.
AUTHOR INFORMATION
Corresponding Author
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(7) For rhodium catalysis, see: Catino, A. J.; Nichols, J. M.; Nettles, B.
J.; Doyle, M. P. J. Am. Chem. Soc. 2006, 128, 5648−5649.
(8) For vanadium catalysis, see: Sud, A.; Sureshkumar, D.; Klussmann,
M. Chem. Commun. 2009, 3169−3171.
Author Contributions
§T.W. performed the synthetic work. M.S. performed the PMP
deprotection.
(9) For platinum catalysis, see: Shu, X.-Z.; Yang, Y.-F.; Xia, X.-F.; Ji, K.-
G.; Liu, X.-Y.; Liang, Y.-M. Org. Biomol. Chem. 2010, 8, 4077−4079.
(10) Muramatsu, W.; Nakano, K.; Li, C.-J. Org. Lett. 2013, 15, 3650−
3653.
Author Contributions
∥A.B. performed the EPR measurements.
Notes
(11) Muramatsu, W.; Nakano, K.; Li, C.-L. Org. Biomol. Chem. 2014,
12, 2189−2192.
The authors declare no competing financial interest.
(12) Singh, K. N.; Kessar, S. V.; Singh, P.; Singh, P.; Kaur, M.; Batra, A.
Synthesis 2014, 46, 2644−2650.
ACKNOWLEDGMENTS
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Generous financial support by the Deutsche Forschungsgemein-
schaft (SFB 813) and the Chinese Scholarship Council (stipend
to T.W.) is gratefully acknowledged.
(13) Essig, S.; Bretzke, S.; Muller, R.; Menche, D. J. Am. Chem. Soc.
̈
2012, 134, 19362−19365.
(14) Compound 8l showed potent inhibitory effects against the P2X3
receptor.
(15) For previous reports on organometallic nucleophilic additions to
THIQs, which are, however, not as general and broadly applicable as the
work described herein, see refs 4g, 5e, 10, 11, and 12.
(16) Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron:
Asymmetry 1999, 10, 221−223.
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