Table 5 Substrate scope of the Brønsted acid differentiated iridium
catalyzed hydrogenation
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iridium complexes were utilized. Racemic complexes were not
investigated. Also see: (d) M. Klussmann, Angew. Chem., Int. Ed.,
2009, 48, 7124–7125.
5 (a) A. Babai and A.-V. Mudring, Inorg. Chem., 2006, 45,
3249–3255; (b) L. Ricard and F. Gagosz, Organometallics, 2007,
26, 4704–4707; (c) O. G. Polyakov, S. M. Ivanova,
C. M. Gaudinski, S. M. Miller, O. P. Anderson and
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C. C. Santini and Y. Chauvin, J. Organomet. Chem., 2008, 693,
2407–2414; (e) C. S. Letko, Z. M. Heiden and T. B. Rauchfuss,
Eur. J. Inorg. Chem., 2009, 4927–4930.
6 Selected important articles on chiral non-coordinating anions in
asymmetric catalysis: (a) J. Lacour and V. Hebbe-Viton, Chem.
Soc. Rev., 2003, 32, 373–382; (b) J. Lacour and D. Moraleda,
Chem. Commun., 2009, 7073–7089; (c) D. B. Llewellyn,
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(d) D. Chen, B. Sundararaju, R. Krause, J. Klankermeyer,
P. H. Dixneuf and W. Leitner, ChemCatChem, 2010, 2, 55–57;
(e) S. P. Smidt, N. Zimmermann, M. Studer and A. Pfaltz,
Chem.–Eur. J., 2004, 10, 4685–4693.
7 Selected articles on iridium(III)–diamine catalysts in asymmetric
reductions: (a) K. Mashima, T. Abe and K. Tani, Chem. Lett.,
1998, 1199–1200; (b) K. Murata, T. Ikariya and R. Noyori, J. Org.
Chem., 1999, 64, 2186–2187; (c) A. Ros, A. Magriz, H. Dietrich,
M. Ford, R. Fernandez and J. M. Lassaletta, Adv. Synth. Catal.,
2005, 347, 1917–1920; (d) T. Ohkuma, N. Utsumi, M. Watanabe,
K. Tsutsumi, N. Arai and K. Murata, Org. Lett., 2007, 9,
2565–2567; (e) X. Wu, J. Liu, X. Li, A. Zanotti-Gerosa,
F. Hancock, D. Vinci, J. Ruan and J. Xiao, Angew. Chem., Int.
Ed., 2006, 45, 6718–6722; (f) Z. M. Heiden and T. B. Rauchfuss,
J. Am. Chem. Soc., 2007, 129, 14303–14310; (g) S.-Y. Shirai,
H. Nara, Y. Kayaki and T. Ikariya, Organometallics, 2009, 28,
802–809; (h) O. Soltani, M. A. Ariger and E. M. Carreira, Org.
Lett., 2009, 11, 4196–4198.
Entrya T/1C
R1 R2
Me
Yieldb e.r.c
1
2
3
4
ꢀ10 4a
H
92
85
96
98
83
77
82
84
71
74
97 : 3
ꢀ10 4b 6-F Me
20 4c 6-Cl Me
20 4d 6-Br Me
20 4e 8-Cl Me
94 : 6
93 : 7
92 : 8
92 : 8
95 : 5
94 : 6
95 : 5
94 : 6
95.5 : 4.5
95 : 5
96 : 4
96 : 4
96 : 4
5
6
7
8
9
10
11
12
13
14
ꢀ10 4f
ꢀ10 4g
ꢀ10 4h
ꢀ10 4i
ꢀ10 4j
ꢀ10 4k
ꢀ10 4l
H
H
H
H
H
H
H
n-Propyl
n-Butyl
n-Pentyl
i-Butyl
–(CH2)2–Ph
–(CH2)2–(3,4-(OMe)2–Ph) 66
–(CH2)2–(3,4-OCH2O–Ph) 72
ꢀ10 4m H
–(CH2)2–(3-OMe–Ph)
–(CH2)2–(4-(Me)–Ph)
81
76
ꢀ10 4n
H
a
Reaction conditions: 0.2 mmol 3a–n, 1.0 mL o-xylene, 1–4 mol% 1b
and 2d, reaction time 24–48 h, reaction temperature as indicated,
b
c
100 bar H2 pressure. Yield of isolated product. Determined by GC
or HPLC on chiral stationary column.
Notes and references
1 (a) Z. Shao and H. Zhang, Chem. Soc. Rev., 2009, 38, 2745–2755;
(b) C. Zhong and X. Shi, Eur. J. Org. Chem., 2010, 2999–3025;
(c) M. Rueping, R. M. Koenigs and J. Atodiresei, Chem. Eur. J.,
2010, DOI: 10.1002/chem.201001140.
8 Selected articles on organocatalytic reductions from our group:
(a) M. Rueping, T. Theissmann and A. P. Antonchick, Synlett,
2006, 1071–1074; (b) M. Rueping, A. P. Antonchick and
T. Theissmann, Angew. Chem., Int. Ed., 2006, 45, 3683–3686;
(c) M. Rueping, A. P. Antonchick and T. Theissmann, Angew.
Chem., Int. Ed., 2006, 45, 6751–6755; (d) M. Rueping and
A. P. Antonchick, Angew. Chem., Int. Ed., 2007, 46, 4562–4565;
(e) M. Rueping, T. Theissmann, S. Raja and J. W. Bats, Adv.
Synth. Catal., 2008, 350, 1001–1006; (f) M. Rueping and
A. P. Antonchick, Angew. Chem., Int. Ed., 2008, 47, 5836–5838;
(g) M. Rueping, F. Tato and F. R. Schoepke, Chem.–Eur. J., 2010,
16, 2688–2691; (h) M. Rueping, E. Sugiono and F. R. Schoepke,
Synlett, 2010, 852–865; (i) M. Rueping and T. Theissmann, Chem.
Sci., 2010, DOI: 10.1039/c0sc00206b.
2 M. Rueping, A. P. Antonchick and C. Brinkmann, Angew. Chem.,
Int. Ed., 2007, 46, 6903–6906.
3 Selected articles: (a) M.-C. Lacasse, C. Poulard and A. B. Charette,
J. Am. Chem. Soc., 2005, 127, 12440–12441; (b) V. Komanduri and
M. J. Krische, J. Am. Chem. Soc., 2006, 128, 16448–16449;
(c) G. L. Hamilton, E. J. Kang, M. Mba and F. D. Toste, Science,
2007, 317, 496–499; (d) S. Mukherjee and B. List, J. Am. Chem.
Soc., 2007, 129, 11336–11337; (e) W. Hu, X. Xu, J. Zhou,
W.-J. Liu, H. Huang, J. Hu, L. Yang and L.-Z. Gong, J. Am.
Chem. Soc., 2008, 130, 7782–7783; (f) X. Xu, J. Zhou, L. Yang and
W. Hu, Chem. Commun., 2008, 6564–6566; (g) K. Sorimachi and
M. Terada, J. Am. Chem. Soc., 2008, 130, 14452–14453;
(h) G. L. Hamilton, T. Kanai and F. D. Toste, J. Am. Chem.
Soc., 2008, 130, 14984–14985; (i) Z.-Y. Han, H. Xiao, X.-H. Chen
and L.-Z. Gong, J. Am. Chem. Soc., 2009, 131, 9182–9183;
(j) X.-Y. Liu and C.-M. Che, Org. Lett., 2009, 11, 4204–4207;
(k) M. Terada and Y. Toda, J. Am. Chem. Soc., 2009, 131,
6354–6355; (l) Y. Lu, T. C. Johnstone and B. A. Arndtsen,
J. Am. Chem. Soc., 2009, 131, 11284–11285; (m) Q. Cai,
Z.-A. Zhao and S.-L. You, Angew. Chem., Int. Ed., 2009, 48,
7428–7431; (n) Q.-W. Zhang, C.-A. Fan, H.-J. Zhang, Y.-Q. Tu,
Y.-M. Zhao, P. Gu and Z.-M. Chen, Angew. Chem., Int. Ed., 2009,
48, 8572–8574; (o) B. Zhao, H. Du and Y. Shi, J. Org. Chem., 2009,
74, 8392–8395; (p) S. Liao and B. List, Angew. Chem., Int. Ed.,
2010, 49, 628–631; (q) R. L. Lalonde, Z. J. Wang, M. Mba,
A. D. Lackner and F. D. Toste, Angew. Chem., Int. Ed., 2010,
49, 598–601; (r) L. Yang, Q. Zhu, S. Guo, B. Qian, C. Xia and
H. Huang, Chem.–Eur. J., 2010, 16, 1638–1645.
9 Selected review articles regarding kinetic discrimination:
(a) K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto,
M. Ueki and R. Angelaud, Angew. Chem., Int. Ed., 2000, 39,
3532–3556; (b) K. Muniz and C. Bolm, Chem.–Eur. J., 2000, 6,
2309–2316; (c) P. J. Walsh, A. E. Lurain and J. Balsells, Chem.
Rev., 2003, 103, 3297–3344; (d) J. W. Faller, A. R. Lavoie and
J. Parr, Chem. Rev., 2003, 103, 3345–3368; (e) K. Mikami and
M. Yamanaka, Chem. Rev., 2003, 103, 3369–3400.
10 Selected articles regarding kinetic discrimination: (a) K. Mikami
and S. Matsukawa, Nature, 1997, 385, 613–615; (b) K. Mikami,
T. Korenaga, M. Terada, T. Ohkuma, T. Pham and R. Noyori,
Angew. Chem., Int. Ed., 1999, 4, 495–497; (c) J. Long and
K. L. Ding, Angew. Chem., Int. Ed., 2001, 40, 544–547;
(d) A. M. Costa, C. Jimeno, J. Gavenonis, P. J. Carroll and
P. J. Walsh, J. Am. Chem. Soc., 2002, 124, 6929–6941;
(e) M. T. Reetz and X. Li, Angew. Chem., Int. Ed., 2005, 44,
2962–2964.
4 (a) C. Li, C. Wang, B. Villa-Marcos and J. Xiao, J. Am. Chem. Soc.,
2008, 130, 14450–14451; (b) C. Li, B. Villa-Marcos and J. Xiao,
J. Am. Chem. Soc., 2009, 131, 6967–6969; (c) B. Villa-Marcos,
c
306 Chem. Commun., 2011, 47, 304–306
This journal is The Royal Society of Chemistry 2011