T. Besset and F. Glorius, J. Am. Chem. Soc., 2011, 133, 2350;
(c) A.-S. Tsai, M. Brasse, R.-G. Bergman and J.-A. Ellman, Org. Lett.,
2011, 13, 540; (d) F.-W. Patureau, T. Besset and F. Glorius, Angew.
Chem., Int. Ed., 2011, 50, 1064; (e) L. Yang, C. A. Correia and C.-J. Li,
Org. Biomol. Chem., 2011, 9, 7176; (f) S. Rakshit, C. Grohmann,
T. Besset and F. Glorius, J. Am. Chem. Soc., 2011, 133, 2350; (g) For a
review, see: T. Satoh and M. Miura, Chem.–Eur. J., 2010, 16, 11212.
4 H. Weissman, X. Song and D. Milstein, J. Am. Chem. Soc., 2001, 123,
337.
S. S. Pandit, Tetrahedron Lett., 2003, 44, 2331; (c) D. Miller,
G. Umbricht, B. Weber and A. Pfaltz, Helv. Chim. Acta, 1991, 74, 232;
(d) C. Bolm, K. Weickhardt, M. Zehnder and T. Ranff, Chem. Ber., 1991,
124, 1173; (e) I. Mohammadpoor-Baltork, A. R. Khosropour and
S. F. Hojati, Synlett, 2005, 2747; (f) K. Schwekendiek and F. Glorius,
Synthesis, 2006, 2996; (g) N. N. Karade, G. B. Tiwari and S.
V. Gampawar, Synlett, 2007, 1921.
11 (a) T. W. Greene and P. G. M. Wutz, Protective Groups in Organic
Synthesis, John Wiley
& Sons, New York, 2nd edn, 1991;
5 (a) C. S. Yi and D. W. Lee, Organometallics, 2009, 28, 4266;
(b) K.-H. Kwon, D. W. Lee and C. S. Yi, Organometallics, 2010, 29,
5748; (c) T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh and
M. Miura, Org. Lett., 2011, 13, 706; (d) L. Ackermann and J. Pospech,
Org. Lett., 2011, 13, 4153; (e) P. B. Arockiam, C. Fischmeister,
C. Bruneau and P. H. Dixneuf, Green Chem., 2011, 13, 3075;
(f) Y. Hashimoto, T. Ueyama, T. Fukutani, K. Hirano, T. Satoh and
M. Miura, Chem. Lett., 2011, 40, 1165.
6 (a) K. Padala and M. Jeganmohan, Org. Lett., 2011, 13, 6144;
(b) K. Padala and M. Jeganmohan, Org. Lett., 2012, 14, 1134; (c) B. Li,
J. Ma, N. Wang, H. Feng, S. Xu and B. Wang, Org. Lett., 2012, 14, 736;
(d) Y. Hashimoto, T. Ortloff, K. Hirano, T. Satoh, C. Bolm and M. Miura,
Chem. Lett., 2012, 41, 151; (e) L. Ackermann, L. Wang, R. Wolfram and
A. V. Lygin, Org. Lett., 2012, 14, 728.
(b) A. I. Meyers and E. D. Mihelich, Angew. Chem., Int. Ed., 1976, 15,
270; (c) T. G. Gant and A. I. Meyers, Tetrahedron, 1994, 50, 2297.
12 S. Oi, E. Aizawa, Y. Ogino and Y. Inoue, J. Org. Chem., 2005, 70,
3113.
13 (a) S. Oi, H. Sato, S. Sugawara and Y. Inoue, Org. Lett., 2008, 10, 1823;
(b) L. Ackermann, A. Althammer and R. Born, Angew. Chem., Int. Ed.,
2006, 45, 2619; (c) L. Ackermann, R. Born and P. Alvarez-Bercedo,
Angew. Chem., Int. Ed., 2007, 46, 6364; (d) L. Ackermann and
M. Mulzer, Org. Lett., 2008, 10, 5043; (e) L. Ackermann, R. Vicente and
A. Althammer, Org. Lett., 2008, 10, 2299.
14 (a) P. B. Arockiam, V. Poirier, C. Fischmeister, C. Bruneau and
P. H. Dixneuf, Green Chem., 2009, 11, 1871; (b) I. Özdemir, S. Demir,
B. Cetinkaya, C. Gourlaouen, F. Maseras, C. Bruneau and P. H. Dixneuf,
J. Am. Chem. Soc., 2008, 130, 1156.
7 (a) R. J. Bergeron, Chem. Rev., 1984, 84, 587; (b) B. S. Davidson, Chem.
Rev., 1993, 93, 1771; (c) M. R. Grimmett, Comprehensive Heterocyclic
Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scvien, Elsevier
Science, Oxford, 1996, vol. 3, pp. 261–318; (d) P. Wipf and
S. Venkatraman, Synlett, 1997, 1; (e) V. S. C. Yeh, Tetrahedron, 2004, 60,
11995.
15 B. Li, K. Devaraj, C. Darcel and P. H. Dixneuf, Tetrahedron, 2012, 68,
5179.
16 L. Ackermann and P. Novak, Org. Lett., 2009, 11, 4966.
17 N. Schröder, T. Besset and F. Glorius, Adv. Synth. Catal., 2012, 354, 579.
18 E. Ferrer-Flegeau, C. Bruneau, P. H. Dixneuf and A. Jutand, J. Am.
Chem. Soc., 2011, 133, 10161.
8 (a) M. Gómez, G. Muller and M. Rocamo, Coord. Chem. Rev., 1999,
193–195, 769; (b) K. M. Engle, T.-S. Mei, M. Wasa and J.-Q. Yu, Acc.
Chem. Res., 2012, 45, 788.
9 For representative reviews, see: (a) G. Desimoni, G. Faita and
K. A. Jørgensen, Chem. Rev., 2006, 106, 3561; (b) L. H. Gade and
S. Bellemin-Laponnaz, Coord. Chem. Rev., 2007, 251, 718;
(c) G. Desimoni, G. Faita and K. A. Jørgensen, Chem. Rev., 2011, 111,
284.
19 F. Pozgan and P. H. Dixneuf, Adv. Synth. Catal., 2009, 351, 1737.
20 L. Ackermann, Chem. Rev., 2011, 111, 1315.
21 The BNPAH acid is stronger than AcOH: it is thus expected to form more
LnRuX+BNPA− and AcOH than LnRuX+AcO− plus BNPAH.
22 The cyclometallated complex (B) (X = Cl) has been isolated and charac-
terized from the reaction of 1a with [RuCl2(p-cymene)]2 and KOAc at
room temperature for 20 h in methanol, see: B. Li, T. Roisnel, C. Darcel
and P. H. Dixneuf, Dalton Trans., 2012, DOI: 10.1039/c2dt31401k. See
also Y. Boutadla, D. L. Davies, R. C. Jones and K. Singh, Chem.–Eur. J.,
2011, 17, 3438.
10 For representative examples: (a) A. Cwik, Z. Hell, A. Hegedüs, Z. Finta
and Z. Horvath, Tetrahedron Lett., 2002, 43, 3985; (b) B. P. Bandgar and
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