5
Tol)3 as the ligand achieved the prevalent formation of the ’-diaryl enamide or the α,β-disubstituted enamide as a single
stereoisomer in all examined cases, respectively. The best activity was observed for oxazolidin-2-one. Further studies are currently
dedicated to test the efficiency and selectivity other reactivities of aryl- and alkylynamides.
Funding Information
This work was financed by the Ministère des Affaires Etrangères et du Développement International and the Università Italo
Francese (Galileo Program G15-69) as well as Erasmus programmes. This work was also supported by the Centre National de la
Recherche Scientifique (CNRS) and the University Côte d’Azur.
Acknowledgments
This work was supported by the Università dell'Aquila, the Centre National de la Recherche Scientifique (CNRS) and the
University Côte d’Azur. This study was partly supported by research funding from the Canceropôle PACA, Institut National du
Cancer and Région Sud. We gratefully acknowledge the Università dell'Aquila for grants to AdN and VM.
Supplementary Material
References and notes
(1) (a) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064. (b) Evano, G.; Coste, A.; Jouvin,
K. Angew. Chem., Int. Ed. 2010, 49, 2840. (c) Evano, G.; Blanchard, N.; Compain, G.; Coste, A.; Demmer, C.S.; Gati, W.; Guissart, C.; Heimburger,
J.; Henry, N.; Jouvin, K.; Karthikeyan, G.; Laouiti, A.; Lecomte, M.; Martin-Mingot, A.; Métayer, B.; Michelet, B.; Nitelet, A.; Theunissen, C.;
Thibaudeau, S.; Wang, J.; Zarca, M.; Zhang, C. Chem. Lett. 2016, 45, 574.
(2) Janousek, Z; Collard, J; Viehe, H. G. Angew. Chem. Int. Ed. Engl. 1972, 11, 917.
(3) (a) A. Coste, G. Karthikeyan, F. Couty, G. Evano, Angew. Chem. Int. Ed. 2009, 48, 4381. (b) K. Jouvin, A. Bayle, F. Legrand, G. Evano, Org. Lett.
2012, 14, 1652.
(4) X.-N. Wang, H.-S. Yeom, L.-C. Fang, S. He, Z.-X. Ma, B. L. Kedrowski, R. P. Hsung, Acc. Chem. Res. 2013, 47, 560.
(5) T. Hamada, X. Ye, S. S. Stahl J. Am. Chem. Soc. 2008, 130, 833.
(6) (a) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776. (b) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426. (c) Zhang,
Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slater, B. W.; Davis, A. Org. Lett. 2005, 7, 1047. (d) Yao, P.-Y.; Zhang, Y.; Hsung, R. P.; Zhao, K. Org.
Lett. 2008, 10, 4275. (e) Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257. (f) Kramer, S.; Dooleweerdt, K.;
Lindhardt, A. T.; Rottländer, M.; Skrydstrup, T. Org. Lett. 2009, 11, 4208. (g) Cao, J.; Xu, Y.; Kong, Y.; Cui, Y.; Hu, Z.; Wang, G.; Deng, Y.; Lai,
G. Org. Lett. 2012, 14, 38. (h) Lam, T. Y.; Wang, Y.-P.; Danheiser, R. L. J. Org. Chem. 2013, 78, 9396. (i) Movassaghi, M.; Hill, M. D.; Ahmad, O.
K. J. Am. Chem. Soc. 2007, 129, 10096. (j) Garcia, P.; Moulin, S.; Miclo, Y.; Leboeuf, D.; Gandon, V.; Aubert, C.; Malacria, M. Chem.-Eur. J. 2009,
15, 2129. (k) Tanaka, R.; Yuza, A.; Watai, Y.; Suzuki, D.; Takayama, Y.; Sato, F.; Urabe, H. J. Am. Chem. Soc. 2005, 127, 7774. (l) Garcia, P.;
Evanno, Y.; George, P.; Sevrin, M.; Ricci, G.; Malacria, M.; Aubert, C.; Gandon, V. Org. Lett. 2011, 13, 2030. (m) Gati, W.; Rammah, M. M.;
Rammah, M. B.; Couty, F.; Evano, G. J. Am. Chem. Soc. 2012, 134, 9078. (n) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao,
P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361. (o) Dooleweerdt, K.; Ruhland, T.; Skrydstrup, T. Org. Lett. 2009, 11, 221. (p) Kong, Y.; Jiang, K.;
Cao, J.; Fu, L.; Yu, L.; Lai, G.; Cui, Y.; Hu, Z.; Wang, G. Org. Lett. 2013, 15, 422.
(7) (a) Yet, L. Chem. Rev. 2003, 103, 4283. (b) Carbery, D. R. Org. Biomol. Chem. 2008, 6, 3455. (c) Evano, G.; Gaumont, A.-C.; Alayrac, C.; Wrona,
I. E.; Giguere, J. R.; Delacroix, O.; Bayle, A.; Jouvin, K.; Theunissen, C.; Gatignol, J.; Silvanus, A. C. Tetrahedron 2014, 70, 1529. (d) Gandon, V.;
Dutta, S.; Mallick, R. K.; Prasad, R.; Sahoo, A. K. Angew. Chem. Int. Ed., 2019, 58, 2289. (e) Gandon, V.; Prabagar, B.; Mallick, R. K.; Prasad, R.;
Sahoo, A. K. Angew. Chem. Int. Ed., 2019, 58, 2365.
(8) Gourdet, B.; Smith, D. L.; Lam, H. W. Tetrahedron 2010, 66, 6026.
(9) (a) Yang, Y.; Wang, L.; Zhang, J.; Jin, Y.; Zhu, G. Chem. Commun. 2014, 50, 2347. (b) Y. Yang, L. Wang, F. Zhang, G. Zhu, J. Org. Chem. 2014,
79, 9319.
(10) (a) Arcadi, A.; Chiarini, M.; Del Vecchio, L.; Marinelli, F.; Michelet, V. Eur. J. Org. Chem. 2017, 16, 2214. (b) Arcadi, A.; M. Chiarini, M.; Del
Vecchio, L.; Marinelli, F.; Michelet, V. Chem. Commun. 2016, 52, 1458. (c) Arcadi, A.; Pietropaolo, E.; Alvino, A.; Michelet, V. Org. Lett. 2013,
15, 2766. (d) Rode, N. D.; Arcadi, A.; Di Nicola, A.; Marinelli, F.; Michelet, V. Org. Lett. 2018, 20, 5103.
(11) (a) Amengual, R.; Genin, E.; Michelet, V.; Savignac, M.; Genêt, J.-P. Adv. Synth. Catal. 2002, 344, 393. (b) Amengual, R.; Michelet, V.; Genet, J.-
P. Tetrahedron Lett. 2002, 43, 5905. (c) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (d) Leseurre, L.; Püntener, K.; Genêt, J.-P.;
Scalone, M.; Michelet, V. Adv. Synth. Catal. 2011, 353, 3269. (e) Leseurre, L.; Le Boucher d’Herouville, F.; Millet, A.; Genêt, J.-P.; Scalone, M.;
Michelet, V. Catal. Commun. 2015, 69, 129.
(12) For selected reviews, see: (a) Li, C.-J. Chem. Rev. 2005, 105, 3095. (b) Pinault, N.; Bruce, D.W. Coord. Chem. Rev. 2003, 241, 1. (c) Lindström, U.
M. Chem. Rev. 2002, 102, 2751. (d) Li, C-J. Chem. Rev. 1993, 93, 2023. (e) Li, C.-J.; Chan, T.H. Tetrahedron 1999, 55, 11149. (f) Lubineau, A.;
Augé, J.; Queneau, Y. Synthesis 1994, 741. (g) Herrmann, W.A.; Kohlpaintner, C.W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
(13) For seminal books, see: (a) Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Aqueous Media Media;Wiley: New York, 1997. (b) Organic Synthesis
in Water Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, Scotland, 1998. (c) Aqueous-Phase Organometallic Catalysis Catalysis; Cornils,
B., Hermann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 1998. (d) Lubineau, A.; Augé, J. in Modern Solvent in Organic Synthesis,Topics in
Current Chemistry, P. Knochel (Ed), Springer-Verlag, Berlin, 1999, 206, 1. (e) Sinou, D. in Modern Solvent in Organic Synthesis, Topics in Current
Chemistry, Knochel, P. (Ed), Springer-Verlag, Berlin, 1999, 206, 41.
(14) (a) Chatt, J.; Ahrland, S.; Davis, N. R.; Williams, A. A. J. Chem. Soc. 1958, 276. (b) E.G. Kuntz, Brevet Allemand N° 2627354, 1976. (c) Michelet,
V.; Savignac, M.; Genêt, J.P. Electronic Encyclopedia of Reagents for Organic Synthesis, Paquette L.; Fuchs, P.; Crich, D.; Wipf, P. Eds, John Wiley
& Sons, 2004. (d) Shaughnessy, K.H. Eur. J. Org. Chem. 2006, 1827.