Fluorinated Alcohols as Solvents for Enantioselective Hydrogenation
UPDATES
[
4] a) B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125,
[11] a) L. Shi, X. Wang, C. A. Sandoval, M. Li, Q. Qi, Z. Li,
K. Ding, Angew. Chem. 2006, 118, 4214–4218; Angew.
Chem. Int. Ed. 2006, 45, 4108–4112; b) P. A. Duckman-
ton, A. J. Blake, J. B. Love, Inorg. Chem. 2005, 44,
7708–7710.
6
608–6609; b) B. Breit, W. Seiche, Pure Appl. Chem.
2
006, 78, 249–256; c) W. Seiche, A. Schuschkowski, B.
Breit, Adv. Synth. Catal. 2005, 347, 1488–1494; d) T.
ˇ
Smejkal, B. Breit, Organometallics 2007, in press; DOI:
0.1002/ejoc.200600849; e) F. Chevallier, B. Breit,
1
[12] Probably these polymeric complexes are responsible
for the low reaction rates. Compare, for example,
Angew. Chem. 2006, 118, 1629–1632; Angew. Chem.
Int. Ed. 2006, 45, 1599–1602.
[11a]
ref.
where such systems have been employed, but
more drastic hydrogenation conditions are required.
13] For other beneficial applications of fluorinated alcohols
in homogeneous catalysis, see: for review: I. A. Shu-
klov, N. V. Dubrovina, A. Bçrner, Synthesis 2007, in
press; a) Mukaiyma–Michael reaction: D. A. Evans,
K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am.
Chem. Soc. 2001, 123, 4480–4491; b) Oxidation: J.-P.
Bꢁguꢁ, D. Bonnet-Delpon, B. Crousse, Synlett 2004,
[
5] B. Breit, W. Seiche, Angew. Chem. 2005, 117, 1666–
[
1
669; Angew. Chem. Int. Ed. 2005, 44, 1640–1643; B.
Breit, Angew. Chem. 2005, 117, 6976–6986; Angew.
Chem. Int. Ed. 2005, 44, 6816–6825.
[
[
6] M. Weis, C. Walloch, W. Seiche, B. Breit, J. Am. Chem.
Soc. 2006, 128, 4188–4189.
7] For a related concept, see: Y. Liu, C. A. Sandoval, Y.
Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J.
Am. Chem. Soc. 2006, 128, 14212–14213.
1
8–29; c) [4+2]cycloaddition: A. Saito, T. Ono, Y.
A
H
R
U
G
Hanzawa, J. Org. Chem. 2006, 71, 6437–6443; in homo-
geneous catalytic hydrogenation, see, e.g.: d) H. Abe,
H. Amii, K. Uneyama, Org. Lett. 2001, 3, 313–315; A.
Suzuki, M. Mae, H. Amii, K. Uneyama, J. Org. Chem.
[8] M.-N. Birkholz, N. V. Dubrovina, H. Jiao, D. Michalik,
J. Holz, R. Paciello, B. Breit, A. Bçrner, Chem. Eur. J.
2
007, 13, 5896–5907.
T
[9] EN values: a) C. Reichardt, Chem. Rev. 1994, 94,
319–2358; b) For MFE: K. Sraïdi, These de Doctorat
2
004, 69, 5132–5134; e) N. V. Dubrovina, V. I. Tararov,
2
A. Monsees, R. Kadyrov, C. Fischer, A. Bçrner, Tetra-
hedron: Asymmetry 2003, 14, 2739–2745; N. V. Dubro-
vina, V. I. Tararov, A. Monsees, A. Spannenberg, I. D.
Kostas, A. Bçrner, Tetrahedron: Asymmetry 2005, 16,
d’Etat, Marrakech, 1986; C. Laurence, M. Berthelot, J.
Graton, in: The Chemisty of Phenols, (Ed.: Z. Rappo-
port), Wiley, Chichester, 2003; pp 529–603; hydrogen
bond acceptor (b) values: c) S. Spange, E. Vilsmeier, S.
Adolph, A. Fährmann, J. Phys. Org. Chem. 1999, 12,
3
640–3649; f) Y. Hsiao, N. R. Rivera, T. Rosner, S. W.
Krska, E. Njolito, F. Wang, Y. Sun, J. D. Armstrong,
E. J. J. Grabowski, R. D. Tillye, F. Spindler, C. Malan, J.
Am. Chem. Soc. 2004, 126, 9918–9919; g) W. Zhang, X.
Zhang, J. Org. Chem. 2007, 72, 1020–1023; h) palla-
dium-catalyzed polymerization: A. Scarel, J. Durand,
D. Franchi, E. Zangrando, G. Mestroni, B. Milani, S.
Gladiali, C. Carfagna, B. Binotti, S. Bronco, T. Gragno-
li, J. Organomet. Chem. 2005, 690, 2106–2120; C. Bian-
chini, A. Meli, W. Oberhauser, A. M. Segarra, C.
Claver, E. J. Garcia Suarez, J. Mol. Catal. A: Chem.
2007, 265, 292–305.
5
47–556; M. J. Kamlet, J. M. Abboud, M. H. Abraham,
R. W. Taft, J. Org. Chem. 1983, 48, 2877–2887; C. Lau-
rence, M. Berthelot, M. Helbert, K. Sraidi, J. Phys.
Chem. 1989, 93, 3799–3802; M. H. Abraham, P. L.
Grellier, D. V. Prior, J. J. Morris, P. J. Taylor, J. Chem.
Soc., Perkin Trans. 2 1990, 521–529.
31
[
10] P NMR data measured for the same complex in
3
1
103
31 31
ACHTREUNG
CDCl : d=54.5 [dd, J( P, Rh)=146 Hz, J( P, P)=
3
3
1
103
31 31
ACHTREUNG
3
3
6 Hz]; d=50.7 [dd, J( P, Rh)=137 Hz, J( P, P)=
6 Hz].
Adv. Synth. Catal. 2007, 349, 2183 – 2187
ꢀ 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2187