10.1002/anie.201708003
Angewandte Chemie International Edition
COMMUNICATION
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.
[10] J. Lu, N. S. Khetrapal, J. A. Johnson, X. C. Zeng, J. Zhang J. Am. Chem.
Soc. 2016, 138, 15805−15808.
[2]
[3]
a) M. Hird, Chem. Soc. Rev. 2007, 36, 2070–2095; b) P. Kirsch, Modern
Fluoroorganic Chemistry, 2nd Edition, Wiley-VCH, 2013.
[11] A. Arꢀvalo, A. Tlahuext-Aca, M. Flores-Alamo, J. J. García, J. Am. Chem.
Soc. 2014, 136, 4634−4639.
Reviews for transition-metal-catalyzed C-F bond formations, see: a) T.
Furuya, J. E. M. N. Klein, T. Ritter, Synthesis 2010, 1804–1821; b) T.
Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470–477; c) C.
Hollingworth, V. Gouverneur, Chem. Commun. 2012, 48, 2929–2942; d)
T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2013, 52,
8214–8264; Angew. Chem. 2013, 125, 8372–8423; e) M. G. Campbell,
T. Ritter, Chem. Rev. 2015, 115, 612−633; f) P. A. Champagne, J.
Desroches, J.-D. Hamel, M. Vandamme, J.-F. Paquin, Chem. Rev. 2015,
115, 9073−9174; and references therein.
[12] a) V. J. Scott, R. Çelenligil-Çetin, O. V. Ozerov, Am. Chem. Soc. 2005,
127, 2852−2853; b) R. Panisch, M. Bolte, T. Müller, J. Am. Chem. Soc.
2006, 128, 9676−9682; c) C. B. Caputo, D. W. Stephan, Organometallics,
2012, 31, 27−30; d) M. Ahrens, G. Scholz, T. Braun, E. Kemnitz, Angew.
Chem. Int. Ed. 2013, 52, 5328–5332; Angew. Chem. 2013, 125, 5436–
5440; e) Related review, see: T. Stahl, H. F. T. Klare, M. Oestreich, ACS
Catal. 2013, 3, 1578–1587.
[13] a) J. Boyer, R. J. P. Corriu, R. Perz, C. Reye, J. Organomet. Chem. 1979,
172, 143−152; b) R. J. P. Corriu, R. Perz,C. Reye, Tetrahedron 1983, 39,
999−1009; c) M. Fujita, T. Hiyama, J. Am. Chem. Soc. 1984, 106,
4629−4630.
[4]
[5]
[6]
G. Balz, G. Schiemann, Ber. Dtsch. Chem. Ges. 1927, 60, 1186–1190.
H. B. Gottlieb, J. Am. Chem. Soc. 1936, 58, 532–533.
Reviews for C-F activations, see: a) J. L. Kiplinger, T. G. Richmond, C.
E. Osterberg, Chem. Rev. 1994, 94, 373–431; b) H. Amii, K. Uneyama,
Chem. Rev. 2009, 109, 2119–2183; c) T. Ahrens, J. Kohlmann, M.
Ahrens, T. Braun, Chem. Rev. 2015, 115, 931–972.
[14] a) C. Blankenship, S. E. Cremer, J. Organomet. Chem. 1989, 371, 19–
30; b) J.-H. Hong, P. Boudjouk, Organometallics 1995, 14, 574–576; c)
N. Rot, T. Nijbacker, R. Kroon, F. J. J. de Kanter, F. Bickelhaupt, M. Lutz,
A. L. Spek, Organometallics 2000, 19, 1319–1324; d) M. J. Bearpark, G.
S. McGrady, P. D. Prince, J. W. Steed, J. Am. Chem. Soc. 2001, 123,
7736−7737
[7]
[8]
Reviews for hydrodefluorinations, see: a) M. F. Kuehnel, D. Lentz, T.
Braun, Angew. Chem. Int. Ed. 2013, 52, 3328–3348; Angew. Chem.
2013, 125, 3412–3433; b) M. K. Whittlesey, E. Peris, ACS Catal. 2014,
4, 3152–3159; c) J.-Y. Hu, J.-L. Zhang, Top Organomet. Chem. 2015,
52, 143–196; and references therein.
[15] P. D. Prince, M. J. Bearpark, G. S. McGrady, J. W. Steed, Dalton Trans.
2008, 271–282.
[16] a) Y. Wang, M. D. Watson, J. Am. Chem. Soc. 2006, 128, 2536−2537;
b) T. Dutta, K. B. Woody, M. D. Watson, J. Am. Chem. Soc. 2008, 130,
452−453.
Selected examples for transition-metal-catalyzed hydrodefluorinations of
polyfluoroarenes, see: a) M. Aizenberg, D. Milstein, Science 1994, 265,
359–361; b) M. Aizenberg, D. Milstein, J. Am. Chem. Soc. 1995, 117,
8674–8675; c) J. Vela, J. M. Smith, Y. Yu, N. A. Ketterer, C. J.
Flaschenriem, R. J. Lachicotte, P. L. Holland, J. Am. Chem. Soc. 2005,
127, 7857–7870; d) T. Braun, J. Izundu, A. Steffen, B. Neumann, H.-G.
Stammler, Dalton Trans. 2006, 5118–5123; e) S. P. Reade, M. F. Mahon,
M. K. Whittlesey, J. Am. Chem. Soc. 2009, 131, 1847–1861; f) T. F.
Beltrán, M. Feliz, R. Llusar, J. A. Mata, V. S. Safont, Organometallics
2011, 30, 290–297; g) W. Zhao, J. Wu, S. Cao, Adv. Synth. Catal. 2012,
354, 574–578; h) P. Fischer, K. Götz, A. Eichhorn, U. Radius,
Organometallics 2012, 31, 1374–1383; i) D. Breyer, T. Braun, P. Klä
ring, Organometallics 2012, 31, 1417–1424; j) J.-H. Zhan, H. Lv, Y. Yu,
J.-L. Zhang, Adv. Synth. Catal. 2012, 354, 1529–1541; k) S. Yow, S. J.
Gates, A. J. P. White, M. R. Crimmin, Angew. Chem. Int. Ed. 2012, 51,
12559−12563; Angew. Chem. 2012, 124, 12727−12731; l) H. Lv, Y.-B.
Cai, J.-L. Zhang, Angew. Chem. Int. Ed. 2013, 52, 3203–3207; Angew.
Chem. 2013, 125, 3285−3289; m) Z. Chen, C.-Y. He, Z. Yin, L. Chen, Y.
He, X. Zhang, Angew. Chem. Int. Ed. 2013, 52, 5813–5817; Angew.
Chem. 2013, 125, 5925−5929; n) J. Li, T. Zheng, H. Suna, X. Li, Dalton
Trans. 2013, 42, 13048–13053; o) T. L. Gianetti, R. G. Bergman, J.
Arnold, Chem. Sci. 2014, 5, 2517–2524; p) M. K. Cybulski, D. McKay, S.
A. Macgregor, M. F. Mahon, M. K. Whittlesey, Angew. Chem. Int. Ed.
2017, 56, 1515–1519; Angew. Chem. 2017, 129, 1537−1541.
[17] a) D. Albanese, D. Landini, M. Penso, Tetrahedron Lett. 1995, 36, 8865–
8866; b) A. Kolomeitsev, G. Bissky, E. Lork, V. Movchun, E. Rusanov, P.
Kirsch, G.-V. Röschenthaler, Chem. Commun. 1999, 1107; c) N.
Maggiarosa, W. Tyrra, D. Naumann, N. V. Kirij, Y. L. Yagupolskii, Angew.
Chem. Int. Ed. 1999, 38, 2252.
[18] a) S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132,
154104–154118; b) S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem.
2011, 32,1456–1465; c) L. Goerigk, S. Grimme, Phys. Chem. Chem.
Phys. 2011, 13, 6670–6688.
[19] The DFT calculations have been conducted using Grimme’s dispersion
correction in order to take into a better account the possibility of the
intermolecular non-covalent interaction. With the optimized structures of
intermediates, the polyfluoroarene or the HDF product are close to one
of the phenyl group attached to the silicon center. When the
combinations of Et2SiH2 with tetrabutylammonoum fluoride (TBAF) or
tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) were
employed, the reactivity was decreased (see Supplementary
Information). These results suggests that the π-π stacking induced by
the phenyl group on silicon center may influence the reactivity.
[20] a) C. N. Neumann, J. M. Hooker, T. Ritter, Nature 2016, 534, 369–373;
b) D. Y. Ong, C. Tejo, K. Xu, H. Hirao, S. Chiba, Angew. Chem. Int. Ed.
2017, 56, 1840–1844; Angew. Chem. 2017, 129, 1866–1870;c) S. D.
Schimler, M. A. Cismesia, P. S. Hanley, R. D. J. Froese, M. J. Jansma,
D. C. Bland, M. S. Sanford, J. Am. Chem. Soc. 2017, 139, 1452−1455.
[9]
S. M. Senaweera, A. Singh, J. D. Weaver, J. Am. Chem. Soc. 2014, 136,
3002−3005.
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