Martina Austeri et al.
FULL PAPERS
e) B. M. Trost, J. Org. Chem. 2004, 69, 5813–5837;
f) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1999, 121,
4545–4554; g) B. M. Trost, D. L. Van Vranken, Chem.
Rev. 1996, 96, 395–422.
b) N. Gurbuz, I. Ozdemir, B. Cetinkaya, J. L. Renaud,
B. Demerseman, C. Bruneau, Tetrahedron Lett. 2006,
47, 535–538; c) B. Demerseman, J. L. Renaud, L.
Toupet, C. Hubert, C. Bruneau, Eur. J. Inorg. Chem.
2006, 1371–1380; d) M. D. Mbaye, B. Demerseman,
J. L. Renaud, C. Bruneau, J. Organomet. Chem. 2005,
690, 2149–2158; e) M. D. Mbaye, B. Demerseman, J. L.
Renaud, L. Toupet, C. Bruneau, Adv. Synth. Catal.
2004, 346, 835–841; f) J. L. Renaud, C. Bruneau, B. De-
merseman, Synlett 2003, 408–410; g) M. D. Mbaye, B.
Demerseman, J. L. Renaud, L. Toupet, C. Bruneau,
Angew. Chem. 2003, 115, 5220–5222; Angew. Chem.
Int. Ed. 2003, 42, 5066–5068; h) S. Gruber, A. B. Zait-
[2] a) G. Helmchen, A. Dahnz, P. Dubon, M. Schelwies, R.
Weihofen, Chem. Commun. 2007, 675–691; b) H.
Miyabe, Y. Takemoto, Synlett 2005, 1641–1655;
c) D. K. Leahy, P. A. Evans, Mod. Rhodium-Catal. Org.
React. 2005, 191–214; d) S. W. Krska, D. L. Hughes,
R. A. Reamer, D. J. Mathre, M. Palucki, N. Yasuda, Y.
Sun, B. M. Trost, Pure Appl. Chem. 2004, 76, 625–633;
e) P. J. Guiry, C. P. Saunders, Adv. Synth. Catal. 2004,
346, 497–537.
¨
[3] a) L. A. Agrofoglio, I. Gillaizeau, Y. Saito, Chem. Rev.
2003, 103, 1875–1916; b) A. Tenaglia, A. Heumann,
Angew. Chem. 1999, 111, 2316–2320; Angew. Chem.
Int. Ed. 1999, 38, 2180–2184.
[4] a) H. He, X. J. Zheng, U. Yi, L. X. Dai, S. L. You, Org.
Lett. 2007, 9, 4339–4341; b) C. Gnamm, S. Fçrster, N.
Miller, K. Brçdner, G. Helmchen, Synlett 2007, 790–
794; c) C. Garcia-Yebra, J. P. Janssen, F. Rominger, G.
Helmchen, Organometallics 2004, 23, 5459–5470.
[5] a) Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo,
S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405–
10406; b) K. Onitsuka, Y. Matsushima, S. Takahashi,
Organometallics 2005, 24, 6472–6474.
sev, M. Worle, P. S. Pregosin, L. F. Veiros, Organometal-
lics 2008, 27, 3796–3805; i) R. Hermatschweiler, I. Fer-
nandez, P. S. Pregosin, F. Breher, Organometallics 2006,
25, 1440–1447; j) I. Fernandez, P. S. Pregosin, A. Albi-
nati, S. Rizzato, Organometallics 2006, 25, 4520–4529;
k) I. Fernandez, R. Hermatschweiler, F. Breher, P. S.
Pregosin, L. F. Veiros, M. J. Calhorda, Angew. Chem.
2006, 118, 6535–6540; Angew. Chem. Int. Ed. 2006, 45,
6386–6391; l) R. Hermatschweiler, I. Fernandez, F.
Breher, P. S. Pregosin, L. F. Veiros, M. J. Calhorda,
Angew. Chem. 2005, 117, 4471–4474; Angew. Chem.
Int. Ed. 2005, 44, 4397–4400; m) H. Kondo, A. Kageya-
ma, Y. Yamaguchi, M.-A. Haga, K. Kirchner, H. Naga-
shima, Bull. Chem. Soc. Jpn. 2001, 74, 1927–1937;
n) H. Kondo, Y. Yamaguchi, H. Nagashima, Chem.
Commun. 2000, 1075–1076; o) T. Kondo, Y. Morisaki,
S.-Y. Uenoyama, K. Wada, T.-A. Mitsudo, J. Am.
Chem. Soc. 1999, 121, 8657–8658; p) T. Kondo, H.
Ono, N. Satake, T.-A. Mitsudo, Y. Watanabe, Organo-
metallics 1995, 14, 1945–1953; q) C. Wang, J. A. Tunge,
Org. Lett. 2005, 7, 2137–2139; r) E. C. Burger, J. A.
Tunge, Chem. Commun. 2005, 2835–2837; s) M. Sapori-
ta, G. Bottari, G. Bruno, D. Drommi, F. Faraone, J.
Mol. Catal. A: Chem. 2009, 309, 159–165.
[6] O. Belda, C. Moberg, Acc. Chem. Res. 2004, 37, 159–
167.
[7] a) A. C. Olson, L. E. Overman, H. F. Sneddon, J. W.
Ziller, Adv. Synth. Catal. 2009, 351, 3186–3192; b) S.
Ueno, J. F. Hartwig, Angew. Chem. 2008, 120, 1954–
1957; Angew. Chem. Int. Ed. 2008, 47, 1928–1931;
c) F. L. Lam, T. T.-L. Au-Yeung, F. Y. Kwong, Z. Zhou,
K. Y. Wong, A. S. C. Chan, Angew. Chem. 2008, 120,
1300–1303; Angew. Chem. Int. Ed. 2008, 47, 1280–
1283; d) S. F. Kirsch, L. E. Overman, N. S. White, Org.
Lett. 2007, 9, 911–913; e) M. Kimura, Y. Uozumi, J.
Org. Chem. 2006, 71, 707–714; f) Y. Uozumi, M.
Kimura, Tetrahedron: Asymmetry 2006, 17, 161–166;
g) I. Lyothier, C. Defieber, E. M. Carreira, Angew.
Chem. 2006, 118, 6350–6353; Angew. Chem. Int. Ed.
2006, 45, 6204–6207; h) C. Shu, J. F. Hartwig, Angew.
Chem. 2004, 116, 4898–4901; Angew. Chem. Int. Ed.
2004, 43, 4794–4797; i) F. Lopez, T. Ohmura, J. F. Hart-
wig, J. Am. Chem. Soc. 2003, 125, 3426–3427; j) B. M.
Trost, W. Tang, Angew. Chem. 2002, 114, 2919–2921;
Angew. Chem. Int. Ed. 2002, 41, 2795–2797; k) P. A.
Evans, D. K. Leahy, J. Am. Chem. Soc. 2002, 124,
7882–7883; l) B. M. Trost, F. D. Toste, J. Am. Chem.
Soc. 2000, 122, 11262–11263.
[12] Y. Matsushima, K. Onitsuka, S. Takahashi, Organome-
tallics 2005, 24, 2747–2754.
[13] M. D. Mbaye, J. L. Renaud, B. Demerseman, C. Bru-
neau, Chem. Commun. 2004, 1870–1871.
[14] K. Onitsuka, H. Okuda, H. Sasai, Angew. Chem. 2008,
120, 1476–1479; Angew. Chem. Int. Ed. 2008, 47, 1454–
1457.
[15] Recently the same group showed that carboxylates are
also effective nucleophiles, see: N. Kanbayashi, K.
Onitsuka, J. Am. Chem. Soc. 2010, 132, 1206–1207.
[16] B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem.
2002, 114, 1101–1103; Angew. Chem. Int. Ed. 2002, 41,
1059–1061.
[8] M. T. Crimmins, J. M. Ellis, K. A. Emmitte, P. A. Haile,
P. J. McDougall, J. D. Parrish, J. L. Zuccarello, Chem.
Eur. J. 2009, 15, 9223–9234.
[17] M. Austeri, D. Linder, J. Lacour, Chem. Eur. J. 2008,
14, 5737–5741.
[18] a) E. P. Kꢅndig, F. R. Monnier, Adv. Synth. Catal. 2004,
346, 901–904; b) A. Mercier, W. C. Yeo, J. Chou, P. D.
Chaudhuri, G. Bernardinelli, E. P. Kundig, Chem.
Commun. 2009, 5227–5229.
[9] V. Farina, J. T. Reeves, C. H. Senanayake, J. J. Song,
Chem. Rev. 2006, 106, 2734–2793.
[10] a) C. Bruneau, J. L. Renaud, B. Demerseman, Chem.
Eur. J. 2006, 12, 5178–5187; b) R. Hermatschweiler, I.
Fernandez, P. S. Pregosin, E. J. Watson, A. Albinati, S.
Rizzato, L. F. Veiros, M. J. Calhorda, Organometallics
2005, 24, 1809–1812.
[19] D. L. Davies, J. Fawcett, S. A. Garratt, D. R. Russell,
Dalton Trans. 2004, 3629–3634.
[20] R. Trivedi, J. A. Tunge, Org. Lett. 2009, 11, 5650–5652.
[21] L. Alcaraz, J. J. Harnett, C. Mioskowski, J. P. Martel, T.
Legall, D. S. Shin, J. R. Falck, Tetrahedron Lett. 1994,
35, 5449–5452.
[11] a) H.-J. Zhang, B. Demerseman, L. Toupet, Z. Xi, C.
Bruneau, Adv. Synth. Catal. 2008, 350, 1601–1609;
3346
ꢃ 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2010, 352, 3339 – 3347