T. Arao et al. / Tetrahedron Letters 48 (2007) 4115–4117
4117
Table 3. Preliminary results of asymmetric version
Ni(cod) (10 mol %)
References and notes
2
1
. Seto, M.; Aramaki, Y.; Imoto, H.; Akiwa, K.; Oda, T.;
Kanzaki, N.; Iizawa, Y.; Baba, M.; Shiraishi, M. Chem.
Pharm. Bull. 2004, 52, 818–829, and references cited
therein.
2. (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int.
Ed. 1998, 37, 3279–3281; (b) Ueda, M.; Miyaura, N. J.
Org. Chem. 2000, 65, 4450–4452.
. Other Rh-catalyzed arylations of aromatic aldehydes with
arylboronic acids: (a) F u¨ rstner, A.; Krause, H. Adv. Synth.
Catal. 2001, 343, 343–350; (b) Moreau, C.; Hague, C.;
Weller, A. S.; Frost, C. G. Tetrahedron Lett. 2001, 42,
(R,R)-Et-Duphos (10 mol %)
OH
Ar'
Arylboroxine (2/3 mol equiv)
Ar-CHO
Ar
NaOt-Bu (0.5 mol equiv)
*
DME/H O=5:1, 100 °C, 48 h
2
a
Entry
Aromatic
aldehyde (Ar=)
Arylboroxine
(Ar =)
Yield
(%)
ee
(%)
0
3
1
2
3
4
5
6
7
1-Naphthyl
1-Naphthyl
Ph
4-Cl–C
Ph
Ph
Ph
Ph
Ph
93
87
91
86
93
83
93
68 (R)
66
78 (R)
74
75
72
6 4
H
2-Me–C
2-Me–4-MeO–C
2-Me–3-F–C
2-Ph–C
4-F–C
6
H
4
6
H
4
6
957–6960; (c) Focken, T.; Rudolph, J.; Bolm, C. Synthe-
6
H
4
sis 2005, 429–436; (d) Suzuki, K.; Ishii, S.; Kondo, K.;
Aoyama, T. Synlett 2006, 648–650; (e) Suzuki, K.; Kondo,
K.; Aoyama, T. Synthesis 2006, 1360–1364; (f) Arao, T.;
Sato, K.; Kondo, K.; Aoyama, T. Chem. Pharm. Bull.
6
H
4
6
H
4
55 (R)
a
Determined by HPLC analysis.
2
006, 54, 1576–1581; (g) Arao, T.; Suzuki, K.; Kondo, K.;
Aoyama, T. Synthesis 2006, 3809–3814.
4
. (a) Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7,
4
153–4155; (b) Suzuki, K.; Arao, T.; Ishii, S.; Maeda, Y.;
ded (1R)-(1-naphthyl)phenylmethanol (2) (48.1 mg,
Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 5789–
9
3%, 68% ee) as a colorless oil. The spectral data were
5792.
2
a
comparable to those reported.
m = 3381 cm
6
1
IR (neat):
. H NMR (CDCl ): d = 2.42 (s, 1H),
5. Takahashi, G.; Shirakawa, E.; Tsuchimoto, T.; Kawa-
kami, Y. Chem. Commun. 2005, 1459–1461.
. Ni-catalyzed alkylation of aldehydes with trialkylborane:
ꢀ1
1
3
6
.48 (s, 1H), 7.21–7.48 (m, 8H), 7.59 (d, J = 7.1 Hz,
1
3
Hirao, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2005, 7,
H), 7.74–7.86 (m, 2H), 7.98–8.02 (m, 1H). C NMR
4
689–4691.
(
CDCl ): d 73.50, 123.86, 124.48, 125.17, 125.44,
3
7
. For recent contributions of Ni-catalyzed addition to
aldehydes, see: (a) Mahandru, G. M.; Liu, G.; Montgo-
mery, J. J. Am. Chem. Soc. 2004, 126, 3698–3699; (b)
Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem.
Soc. 2003, 125, 3442–3443.
1
1
1
8
25.98, 126.90, 127.48, 128.29, 128.35, 128.60, 130.54,
33.75, 138.63, 142.94. EIMS: m/z = 234 (M ), 217,
+
57, 129, 128, 105, 77. Anal. Calcd for C H O: C,
1
7
14
7.15; H, 6.02. Found: C, 86.95; H, 5.99. The ee was
determined by HPLC analysis with Daicel Chiralcel
OD-H (eluent: hexane/i-PrOH, flow: 1.0 mL/min). The
absolute configuration was determined by comparison
8. For the results of Ni sources and ligands screened, see:
Table SI-1 (Supplementary data).
9
. For details, see: Tables SI-2 and SI-3 (Supplementary
2
a
data).
of the reported specific rotation.
2
1
0. g -Coordinated nickel complexes with aldehydes have
been reported: (a) Ogoshi, S.; Oka, M.; Kurosawa, H. J.
Am. Chem. Soc. 2004, 126, 11802–11803; (b) Ogoshi, S.;
Kamada, H.; Kurosawa, H. Tetrahedron 2006, 62, 7583–
Acknowledgements
7
588.
We thank the Ministry of Education, Culture, Sports,
Science and Technology, Japan, for support. K.K. was
financially supported by the Takeda Science
Foundation.
1
1. For a quite recent review, see: Schmidt, F.; Stemmler, R.
T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454–
471.
12. (a) Tomita, D.; Wada, R.; Kanai, M.; Shibasaki, M. J.
Am. Chem. Soc. 2005, 127, 4138–4139; (b) Tomita, D.;
Kanai, M.; Shibasaki, M. Chem. Asian. J. 2006, 1–2, 161–
1
66.
3. Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124,
4850–14851.
Supplementary data
1
1
1
4. For new tuned Duphos derivatives, see: Oisaki, K.; Zhao,
D.; Suto, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett.
2005, 46, 4325–4329.