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FULL PAPER
[
[
15] For a review on zwitterionic catalysts, see: M. Stradiotto, K. D.
Hesp, R. J. Lundgren, Angew. Chem. Int. Ed. 2010, 49, 494;
Angew. Chem. 2010, 122, 504.
Acknowledgments
The Centre National de la Recherche Scientifique (CNRS) is grate-
fully acknowledged for financial support.
16] a) S. Kronig, E. Theuergarten, C. G. Daniliuc, P. G. Jones, M.
Tamm, Angew. Chem. Int. Ed. 2012, 51, 3240; Angew. Chem.
2012, 124, 3294; for other examples of NHCs featuring weakly
coordinating anions, see: b) E. L. Kolychev, S. Kronig, K.
Brandhorst, M. Freytag, P. G. Jones, M. Tamm, J. Am. Chem.
Soc. 2013, 135, 12448; c) A. El-Hellani, V. Lavallo, Angew.
Chem. Int. Ed. 2014, 53, 4489; d) M. J. Asay, S. P. Fisher, S. E.
Lee, F. S. Tham, D. Borchardt, V. Lavallo, Chem. Commun.
[
1] For monographs, see: a) Gold Catalysis, An Homogeneous Ap-
proach (Eds.: F. D. Toste, V. Michelet), Imperial College Press,
London, 2014; b) Modern Gold Catalyzed Synthesis (Eds.:
A. S. K. Hashmi, F. D. Toste), Wiley–VCH, Weinheim, 2012.
2] For a general, recent overview, see: a) C. M. Friend, A. S. K.
Hashmi, Acc. Chem. Res. 2014, 47, 729; for selected general
reviews, see: b) Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108,
[
2015, 51, 5359.
[
[
17] a) V. Lavallo, J. H. Wright, F. S. Tham, S. Quinlivan, Angew.
Chem. Int. Ed. 2013, 52, 3172; Angew. Chem. 2013, 125, 3254;
for another example of a transition metal complex supported
by a phosphine containing a weakly coordinating carborane
anion, see: b) A. El-Hellani, C. E. Kefalidis, F. S. Tham, L.
Maron, V. Lavallo, Organometallics 2013, 32, 6887.
3239; c) D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008,
108, 3351; d) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395;
e) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180; f) A. S. K.
Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896;
Angew. Chem. 2006, 118, 8064.
18] M. Devillard, E. Nicolas, C. Appelt, J. Backs, S. Mallet-Lad-
eira, G. Bouhadir, J. C. Slootweg, W. Uhl, D. Bourissou, Chem.
Commun. 2014, 50, 14805.
[
3] For selected recent reviews, see: a) L. Fensterbank, M. Malac-
ria, Acc. Chem. Res. 2014, 47, 953; b) A. Fürstner, Acc. Chem.
Res. 2014, 47, 925; c) C. Obradors, A. M. Echavarren, Acc.
Chem. Res. 2014, 47, 902; d) S. P. Nolan, Acc. Chem. Res. 2011, [19] V. César, N. Lugan, G. Lavigne, J. Am. Chem. Soc. 2008, 130,
4
5
4, 91; e) A. S. K. Hashmi, Angew. Chem. Int. Ed. 2010, 49,
11286.
232; Angew. Chem. 2010, 122, 5360; f) V. Michelet, P. Y. Toul- [20] V. César, N. Lugan, G. Lavigne, Chem. Eur. J. 2010, 16, 11432.
lec, J.-P. Genêt, Angew. Chem. Int. Ed. 2008, 47, 4268; Angew.
Chem. 2008, 120, 4338.
[21] V. César, L. C. Misal Castro, T. Dombray, J.-B. Sortais, C. Dar-
cel, S. Labat, K. Miqueu, J.-M. Sotiropoulos, R. Brousses, N.
Lugan, G. Lavigne, Organometallics 2013, 32, 4643.
[4] a) M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2011, 47,
6536; b) N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994.
[22] V. César, C. Barthes, Y. C. Farré, S. V. Cuisiat, B. Y. Vacher, R.
Brousses, N. Lugan, G. Lavigne, Dalton Trans. 2013, 42, 7373.
[23] D. Tapu, Z. McCarty, C. McMillen, Chem. Commun. 2014, 50,
4725.
[24] a) M. V. Baker, P. J. Barnard, S. J. Berners-Price, S. K. Bray-
shaw, J. L. Hickey, B. W. Skelton, A. H. White, J. Organomet.
Chem. 2005, 690, 5625; b) M. V. Baker, P. J. Barnard, S. K.
Brayshaw, J. L. Hickey, B. W. Skelton, A. H. White, Dalton
Trans. 2005, 37; c) P. de Frémont, N. M. Scott, E. D. Stevens,
S. P. Nolan, Organometallics 2005, 24, 2411.
[5] a) Y. Zhang, T. Luo, Z. Yang, Nat. Prod. Rep. 2014, 31, 489;
b) M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41,
2
448; c) A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008,
37, 1766.
[
6] a) D. Wang, R. Cai, S. Sharma, J. Jirak, S. K. Thummanapelli,
N. G. Akhmedov, H. Zhang, X. Liu, J. L. Petersen, X. Shi, J.
Am. Chem. Soc. 2012, 134, 9012; b) A. Homs, I. Escofet, A. M.
Echavarren, Org. Lett. 2013, 15, 5782; c) Y. Zhu, C. S. Day, L.
Zhang, K. J. Hauser, A. C. Jones, Chem. Eur. J. 2013, 19,
12264; d) D. Weber, M. R. Gagné, Org. Lett. 2009, 11, 4962;
[25] Complex 3·NEt
4
crystallizes with two independent molecules
e) C. Nevado, A. M. Echavarren, Chem. Eur. J. 2005, 11, 3155;
f) S. R. Patrick, I. I. F. Boogaerts, S. Gaillard, A. M. Z. Slawin,
S. P. Nolan, Beilstein J. Org. Chem. 2011, 7, 892; g) H. Li, R. A.
Widenhoefer, Org. Lett. 2009, 11, 2671; h) M. A. Tarselli, A. R.
Chianese, S. J. Lee, M. R. Gagné, Angew. Chem. Int. Ed. 2007,
in the asymmetric unit displaying similar geometrical data.
[26] J. J. Dunsford, K. J. Cavell, B. M. Kariuki, Organometallics
2012, 31, 4118.
[27] C. Nieto-Oberhuber, M. Paz Muñoz, S. López, E. Jiménez-
Núñez, C. Nevado, E. Herrero-Gómez, M. Raducan, A. M.
Echavarren, Chem. Eur. J. 2006, 12, 1677.
[28] V. César, S. Labat, K. Miqueu, J.-M. Sotiropoulos, R. Brousses,
N. Lugan, G. Lavigne, Chem. Eur. J. 2013, 19, 17113.
[29] G. R. Fulmer, A. J. M. Miller, N. H. Sherden, H. E. Gottlieb,
A. Nudelman, B. M. Stoltz, J. E. Bercaw, K. I. Goldberg, Orga-
nometallics 2010, 29, 2176.
[30] R. Usón, A. Laguna, M. Laguna, Inorg. Synth. 1989, 26, 85.
[31] a) R. Visbal, A. Laguna, M. C. Gimeno, Chem. Commun. 2013,
49, 5642; b) A. Collado, A. Gómez-Suárez, A. R. Martin,
A. M. Z. Slawin, S. P. Nolan, Chem. Commun. 2013, 49, 5541.
[32] a) J. W. Faller, P. P. Fontaine, J. Organomet. Chem. 2006, 691,
1912. For the synthesis of the dimethyl propargylmalonate, see:
b) K. H. Dötz, M. Popall, Tetrahedron 1985, 41, 5797.
[33] W. Wang, J. Yang, F. Wang, M. Shi, Organometallics 2011, 30,
3859.
46, 6670; Angew. Chem. 2007, 119, 6790.
[
[
[
7] For a review on silver-free gold catalysts, see: H. Schmidbaur,
A. Schier, Z. Naturforsch. B 2011, 66, 329.
8] See, for example: J. H. Teles, S. Brode, M. Chabanas, Angew.
Chem. Int. Ed. 1998, 37, 1415; Angew. Chem. 1998, 110, 1475.
9] S. Gaillard, J. Bosson, R. S. Ramón, P. Nun, A. M. Z. Slawin,
S. P. Nolan, Chem. Eur. J. 2010, 16, 13729.
[
[
10] M. T. Reetz, K. Sommer, Eur. J. Org. Chem. 2003, 3485.
11] K. D. Hesp, M. Stradiotto, J. Am. Chem. Soc. 2010, 132,
18026.
[
12] a) V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleilhavoup, G.
Bertrand, Angew. Chem. Int. Ed. 2008, 47, 5224; Angew. Chem.
2008, 120, 5302; b) X. Zeng, R. Kinjo, B. Donnadieu, G. Ber-
trand, Angew. Chem. Int. Ed. 2010, 49, 942; Angew. Chem.
010, 122, 954.
2
[
[
13] V. Lavallo, G. D. Frey, S. Kousar, B. Donnadieu, G. Bertrand,
Proc. Natl. Acad. Sci. USA 2007, 104, 13569.
[34] L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837–838.
[35] A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J.
Appl. Crystallogr. 1993, 26, 343–350.
[36] G. M. Sheldrick, Acta Crystallogr., Sect. A: Fundam. Crys-
tallogr. 2008, 64, 112–122.
14] a) W. Fang, M. Presset, A. Guérinot, C. Bour, S. Bezzenine-
Lafollée, V. Gandon, Chem. Eur. J. 2014, 20, 5439; b) A. Guéri-
not, W. Fang, M. Sircoglou, C. Bour, S. Bezzenine-Lafollée, V.
Gandon, Angew. Chem. Int. Ed. 2013, 52, 5848; Angew. Chem.
Received: February 16, 2015
Published Online: March 31, 2015
2013, 125, 5960.
Eur. J. Inorg. Chem. 2015, 2216–2221
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