10.1002/adsc.201900268
Advanced Synthesis & Catalysis
Slaughter), Springer: Berlin, 2015; e) M. Brill, S. P.
3700–3708; Y. Liu, X. Chen, J. Zhang, Z. Xu, Synlett
2013, 24, 1371–1376.
Nolan, Top. Organomet. Chem. 2018, 62, 51-90.
[2] a) D. J. Gorin, B. D Sherry, F. D. Toste, Chem. Rev.
2008, 108, 3351-3378; b) A. S. K. Hashmi, Chem. Rev.
2007, 107, 3180-3211; c) K. Chen, S. Zhu, Synlett, 2017,
28, 640-653; d) A. Simonneau, Y. Harrak, L. Jeanne-
Julien, G. Lemière, V. Mouriès-Mansuy, J. -P. Goddard,
M. Malacria, L. Fensterbank, ChemCatChem, 2013, 5,
1096-1099; e) A. Corma, A. Leyva-Pꢀrez, M. J. Sabater,
Chem. Rev. 2011, 111, 1657-1712; f) H. Wei, M. Bao,
K. Dong, L. Qiu, B. Wu, W. Hu, X. Xu, Angew. Chem.
2018, 130, 17446-17450; g) H. C. Shen, Tetrahedron
2008, 64, 7847−7870; h) F. Schröder, C. Tugny, E.
Salanouve, H. Clavier, L. Giordano, D. Moraleda, Y.
Gimbert, V. Mouriès-Mansuy, J.-P. Goddard, L.
Fensterbank, Organometallics, 2014, 33, 4051-4056.
[3] a) V. A. Soloshonok, T. Hayashi, Tetrahedron Lett.
1994, 35, 2713−2716; b) G. T. Giuffredi, B. Bernet, V.
Gouverneur, V. Eur. J. Org. Chem. 2011, 2011,
3825−3836; c) Q. Wang, Y. Jiang, R. Sun, X. Y. Tang,
M. Shi, Chem. Eur. J. 2016, 22, 14739-14745.
[4] a) K. Müller, C. Faeh, F. Diederich, Science 2007, 317,
1881-1886; b) S. Purser, P. R. Moore, S. Swallow, V.
Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330; c) S.
M. Ametamey, M. Honer, P. A. Schubiger, Chem. Rev.
2008, 108, 1501-1516; d) V. Gouverneur, K. Seppelt,
Chem. Rev. 2015, 115, 563-565; e) D. E. Yerien, S.
Bonesi, A. Postigo, Org. Biomol. Chem. 2016, 14, 8398-
8427; f) Y. Zhou, J. Wang, Z. Gu, S. Wang, W. Zhu, J.
L. Aceꢁa, V. A. Soloshonok, K. Izawa, H. Liu, Chem.
Rev. 2016, 116, 422−518.
[11] a) E. Tomas-Mendivil, C. Heinrich, J. C. Ortuno, J.
Starck, V. Michelet, ACS Catal. 2017, 7, 380-387; b) G.
Mariaule, G. Newsome, P. Y. Toullec, P. Belmont, V.
Michelet, Org. Lett. 2014, 16, 4570-4573.
[12] a) A. Arcadi, E. Pietropaolo, A. Alvino, V. Michelet,
Beilstein J. Org. Chem. 2014, 10, 449-458; b) A. Arcadi,
E. Pietropaolo, A. Alvino, V. Michelet, Org. Lett. 2013,
15, 2766-2769.
[13] a) P. Nun, R. S. Ramón, S. Gaillard, S. P. Nolan, J.
Organomet. Chem. 2011, 696, 7-11; b) N. Marion, R. S.
Ramón, S. P. Nolan, J. Am. Chem. Soc. 2009, 131, 448-
449.
[14] a) G. Stavber, M. Zupan, S. Stavber, Synlett, 2009,
589-594; b) T. Kitamura, K. Muta, K. Muta, J. Org.
Chem., 2014, 79, 5842-5846; c) S. Stavber, M. Jereb, M.
Zupan, Synthesis, 2002, 2609-2615.
[15] a) N. T. Patil, Y. Yamamoto, J. Org. Chem. 2004, 69,
5139−5142; b) N. Asao, T. Nogami, K. Takahashi, Y.
Yamamoto, J. Am. Chem. Soc. 2002, 124, 764-765; c) T.
Godet, C. Vaxelaire, C. Michel, A. Milet, P. Belmont,
Chem. - Eur. J. 2007, 13, 5632-5641; d) M. Dell’Acqua,
D. Facoetti, G. Abbiati, E. Rossi, Synthesis 2010, 2367-
2378; e) E. Parker, N. Leconte, T. Godet, P. Belmont,
Chem. Commun. 2011, 47, 343-345; f) X. Bantreil, C.
Vaxelaire, T. Godet, E. Parker, C. Sauer, P. Belmont,
Org. Biomol. Chem. 2011, 9, 4831-4841; g) M.
Dell’Acqua, B. Castano, C. Cecchini, T. Pedrazzini, V.
Pirovano, E. Rossi, A. Caselli, G. Abbiati, J. Org. Chem.
2014, 79, 3494-3505.
[5] a) J. Miró, C. del Pozo, Chem. Rev. 2016, 116, 11924-
11966; b) P. A. Sibbald, F. E. Michael, Org. Lett. 2009,
11, 1147-1149; c) P. T. Nyffeler, S. G. Durón, M. D.
Burkart, S. P. Vincent, C. H. Wong, Angew. Chem. Int.
Ed. 2005, 44, 192-212.
[6] M. Schuler, F. Silva, C. Bobbio, A. Tessier, V.
Gouverneur, Angew. Chem. Int. Ed. 2008, 47,
7927−7930.
[7] a) M. N. Hopkinson, A. D. Gee, V. Gouverneur, Chem.
Eur. J. 2011, 17, 8248-8262; b) S. Zhu, Z. Zhang, X.
Huang, H. Jiang, Z. Guo, Chem. Eur. J. 2013, 19, 4695-
4700; c) A. Simonneau, P. Garcia, J. P. Goddard, V.
Mouriès-Mansuy, M. Malacria, L. Fensterbank,
Beilstein J. Org. Chem. 2011, 7, 1379-1386; d) C. Geng,
R. Zhu, M. Li M, T. Lu, S. E. Wheeler, C. Liu, Chem.
Eur. J. 2014, 20, 15833-15839.
[16] a) K. M. Engle, T. S. Mei, X. Wang, J. Q. Yu, Angew.
Chem., Int. Ed. 2011, 50, 1478-1491; (b) H. A. Wegner,
M. Auzias, Angew. Chem., Int. Ed. 2011, 50, 8236-
8247; c) N. Aso, K. Sato, Org. Lett. 2006, 8, 5361-5363;
d) N. Asao, H. Aikawa, S. Tago, K. Umetsu, Org. Lett.
2007, 9, 4299-4302.
[17] a) S. Zhu, H. Huang, Z. Zhang, T. Ma, H. Jiang, J. Org.
Chem. 2014, 79, 6113-6122; b) N. Asao, T. Kasahara, Y.
Yamamoto, Angew. Chem. 2003, 115, 3628-3630; c) X.
Zhao, X. G. Zhang, R. Y. Tang, C. L. Deng, J. H. Li, Eur.
J. Org. Chem. 2010, 4211-4217; d) G. Dyker, D.
Hildebrandt, J. Liu, K. Merz, Angew. Chem. Int. Ed.
2003, 42, 4399-4402.
[18] a) G. Zhang, L. Cui, Y. Wang, L. Zhang, J. Am. Chem.
Soc. 2010, 132, 1474-1475; b) W. E. Brenzovich Jr., D.
Benitez, A. D. Lackner, H. P. Shunatona, E. Tkatchouk,
W. A. Goddard III, F. D. Toste, Angew. Chem. Int. Ed.
2010, 49, 5519-5522.
[8] T. de Haro, C. Nevado, Adv. Synth. Catal. 2010, 352,
2767-2772.
[9] W. B. Wang, J. Jasinski, G. B. Hammond, B. Xu, Angew.
Chem. Int. Ed. 2010, 49, 7247-7252.
[19] a) J. Santhi, B. Baire, ChemistrySelect, 2017, 2, 4338-
4342; b) X. Bantreil, A. Bourderioux, P. Mateo, C. E.
Hagerman, M. Selkti, E. Brachet, P. Belmont, Org. Lett.
2016, 18, 4814-4817; c) Y. Madich, R. Álvarez, J. M.
Aurrecoechea, Eur. J. Org. Chem. 2014, 6263–6271;
d)R. X. Wang, S. T. Yuan, J. B. Liu, J. Wu, G. Qiu, Org.
Biomol. Chem., 2018, 16, 4501-4508; e) M. Bian, W.
Yao, H. Ding, C. Ma, J. Org. Chem. 2010, 75, 1, 269-
272; f) G. Liu, Y. Zhou, D. Ye, D. Zhang, X. Ding, H.
Jiang, H. Liu, Adv. Synth. Catal. 2009, 351, 2605-2610.
[20] Fustero, I. Ibáñez, P. Barrio, M. A. Maestro, S. Catalián,
Org. Lett. 2013, 15, 4, 832-835
[10] a) For a recent reported on silver-catalyzed reaction of
carbonyl-yne, using NFSI as fluorinating reagents in
dioxane at 50 °C, see. F. H. Li, Z. J. Cai, L. Yin, J. Li, S.
Y. Wang, S. J. Ji, Org. Lett. 2017, 19, 1662−1665. b) For
recent contributions on the synthesis of -fluoroketones,
see: X. Zeng, S. Liu, G. B. Hammond, B. Xu, Chem.
Eur. J. 2017, 23, 11977–11981; Z. Jin, R. S. Hidinger,
B. Xu, G. B. Hammond, J. Org. Chem. 2012, 77, 7725-
7729; X. Chen, Y. Zhou, M. Hong, Y. Ling, D. Yin, S.
Wang, X. Zhang, W. Rao, Adv. Synth. Catal. 2018, 360,
6
This article is protected by copyright. All rights reserved.