Organic Letters
Experimental procedures and NMR spectra (PDF)
Letter
Michelet, V. Adv. Synth. Catal. 2008, 350, 2401. (f) Pradal, A.; Gladiali,
S.; Michelet, V.; Toullec, P. Y. Chem. - Eur. J. 2014, 20, 7128.
(11) (a) Tanaka, K.; Otake, Y.; Sagae, H.; Noguchi, K.; Hirano, M.
Angew. Chem., Int. Ed. 2008, 47, 1312. (b) Tsuchikama, K.; Kuwata, Y.;
Tahara, Y.-K.; Yoshinami, Y.; Shibata, T. Org. Lett. 2007, 9, 3097.
(12) (a) Santhoshkumar, R.; Mannathan, S.; Cheng, C.-H. Org. Lett.
2014, 16, 4208. (b) Santhoshkumar, R.; Mannathan, S.; Cheng, C.-H. J.
Am. Chem. Soc. 2015, 137, 16116.
AUTHOR INFORMATION
Corresponding Author
■
Author Contributions
†R.L. and Z.N. contributed equally.
Notes
(13) (a) Evans, P. A.; Sawyer, J. R.; Lai, K. W.; Huffman, J. C. Chem.
Commun. 2005, 3971. (b) Shibata, T.; Arai, Y.; Tahara, Y.-K. Org. Lett.
2005, 7, 4955.
The authors declare no competing financial interest.
(14) For selected recent reviews, see: (a) Garcia-Garrido, S. E. In
Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations;
Trost, B. M., Li, C.-J., Eds.; Wiley-VCH: Weinheim, 2015; p 301.
(b) Trost, B. M.; Masters, J. T. Chem. Soc. Rev. 2016, 45, 2212.
(15) (a) Transition-Metal-Mediated Aromatic Ring Construction;
Tanaka, K., Ed.; Wiley: Hoboken, 2013. (b) Alexandrovna, M. I.;
Ionin, B. I.; Tebby, J. C. Alkynes in Cycloadditions; Wiley: Chichester,
2014; pp 5−105.
(16) (a) Ogata, K.; Murayama, H.; Sugasawa, J.; Suzuki, N.; Fukuzawa,
S.-i. J. Am. Chem. Soc. 2009, 131, 3176. (b) Shibata, Y.; Tanaka, K. Angew.
Chem., Int. Ed. 2011, 50, 10917.
(17) (a) Ogata, K.; Sugasawa, J.; Atsuumi, Y.; Fukuzawa, S.-i. Org. Lett.
2010, 12, 148. (b) Ogata, K.; Sugasawa, J.; Fukuzawa, S.-i. Angew. Chem.,
Int. Ed. 2009, 48, 6078.
ACKNOWLEDGMENTS
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We thank the CNRS and MESR for financial support. R.L. and
Z.N. are grateful for Ph.D. fellowships from the China
Scholarship Council (CSC). We thank Dr. I. DeRiggi (ECM)
for help with the NMR spectra analysis and Dr. A. Vasseur
(ECM) for fruitful discussions.
DEDICATION
■
This paper is dedicated to Professor Barry M. Trost (Stanford
University) on the occasion of his 75th birthday.
(18) (a) Ogata, K.; Sugasawa, J.; Atsuumi, Y.; Fukuzawa, S.-i. Org. Lett.
2010, 12, 148. (b) Hoshino, Y.; Shibata, Y.; Tanaka, K. Angew. Chem.,
Int. Ed. 2012, 51, 9407. (c) Hara, J.; Ishida, M.; Kobayashi, M.; Noguchi,
K.; Tanaka, K. Angew. Chem., Int. Ed. 2014, 53, 2956.
(19) The exact role of the propargylic methyl substituents remains to
be established. A working hypothesis rests upon the hyperconjugation in
intermediate B (Scheme 8), which might favor the σ-bond metathesis
step (intermediate C).
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