Z. Liu, M. Shi / Tetrahedron: Asymmetry 20 (2009) 119–123
123
2
D
0
CHCl
14:0 (c 0.212, CHCl
N-[(2,3-Dichlorophenyl)-(1H-indol-3-yl)-methyl]-4-methylben-
zenesulfonamide 3h: Mp 103–105 °C; IR (KBr) 3385, 3281,
919, 2837, 1594, 1461, 1342, 1158, 1091, 810, 740, 662 cm
3
), 71% yield. Compound 3g (catalyzed by 1c): ꢀ66% ee, ½
a
ꢁ
¼
596; (d) Sundberg, R. J. In The Chemistry of Indoles; Academic: New York, 1996;
pp 105–118.
ꢀ
3
), 74% yield.
2
.
Sundberg, R. J., Indoles, Academic Press: New York, 1996; Chapter 11, pp 105–
118.
m
3. (a) Johannsen, M. Chem. Commun. 1999, 2233–2234; (b) Jia, Y. X.; Xie, J. H.;
Duan, H. F.; Wang, L. X.; Zhou, Q. L. Org. Lett. 2006, 8, 1621–1624; (c) Wang, Y.-
Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156–8157; (d)
Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484–1485.
ꢀ1
2
;
1
6 3
H NMR (acetone-d , 300 MHz): d 2.39 (3H, s, CH ), 6.33 (1H, d,
J = 7.8 Hz, NH), 6.66 (1H, d, J = 1.8 Hz, CH), 6.96 (1H, t, J = 7.5 Hz,
Ar), 7.12 (1H, t, J = 7.6 Hz, Ar), 7.23–7.30 (5H, m, Ar), 7.37 (1H, d,
J = 8.1 Hz, Ar), 7.43 (1H, d, J = 8.1 Hz, Ar), 7.65–7.71 (3H, m, Ar),
4. (a) Kim, Y. H. Acc. Chem. Res. 2001, 34, 955–962; (b) Zanoni, G.; Castronovo, F.;
Franzini, M.; Vidari, G.; Giannini, E. Chem. Soc. Rev. 2003, 32, 115–129; (c)
Kobayashi, S.; Hirobe, M. J. Am. Chem. Soc. 1994, 116, 9805–9806;; (d) Altava, B.;
Burguete, M. I.; GarcLa-Verdugo, E.; Luis, S. V.; Miravet, J. F.; Vicent, M. J.
Tetrahedron: Asymmetry 2000, 11, 4885–4893; (e) Altava, B.; Burguete, M. I.;
GarcLa-Verdugo, E.; Luis, S. V.; Vicent, M. J. Green Chem. 2006, 8, 717–726; (f)
Altava, B.; Burguete, M. I.; Fraile, J. M.; GarcLa, J. I.; Mayoral, J. A.; Luis, S. V.;
Vicent, M. J. Angew. Chem., Int. Ed. 2000, 39, 1503–1506; (g) Kato, N.; Mita, T.;
Kanai, M.; Therrien, B.; Kawano, M.; Yamaguchi, K.; Danjo, H.; Sei, Y.; Sato, A.;
Furusho, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768–6769; (h) Burguete,
M. I.; Collado, M.; Escorihuela, J.; Luis, S. V. Angew. Chem., Int. Ed. 2007, 46, 9002–
1
1
1
(
C
0.19 (1H, s, NH). 1 C NMR (acetone-d
3
6
, 75 MHz): d 21.2, 52.7,
12.2, 114.6, 119.5, 119.9, 122.6, 125.1, 126.8, 127.7, 128.1,
28.3, 129.5, 130.0, 131.1, 132.9, 137.6, 139.1, 142.6, 143.6; MS
EI) m/e 444.0 (M ), 238.0 (M -206, 100); HRMS (EI) calcd for
SCl requires 444.0466, found 444.0466. Enantiomeric
excess was determined by HPLC with a Chiralcel OD-H column
+
+
22
H
18
N
2
O
2
2
9005.
i
(
1
hexane/ PrOH = 70/30, 0.7 mL/min, 254 nm,
t
R
= 6.68 and
5. (a) Bourisou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39–
92; (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290–1309; (c) Hillier,
A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet.
Chem. 2002, 653, 69–82; (d) Clavier, H.; Nolan, S. P. Annu. Rep. Prog. Chem., Sect. B
2007, 103, 193–222; (e) Glorius, F.; Stahl, S. S.; Nolan, S. P.; Peris, E.; Bellemin-
Laponnaz, S.; Louie, J.; Ritter, T. Top. Organomet. Chem. 2007, 21, 1–218.
2
D
0
5.73 min); 3h (catalyzed by 1a): 30% ee, ½
aꢁ
¼ ꢀ16:4 (c 0.5,
CHCl ), 71% yield. Compound 3h (catalyzed by 1c): 60% ee,
3
20
½
a
ꢁ
¼ ꢀ25:3 (c 0.35, CHCl
3
), 78% yield.
D
Compound 4: This is a known compound. 1H NMR (CDCl
8
3
6.
(a) Hiraki, K.; Onishi, M.; Sugino, K. J. Organomet. Chem. 1979, 171, C50–C52; (b)
Hiraki, K.; Sugino, K. J. Organomet. Chem. 1980, 201, 469–475; (c) Frey, G. D.; Jan
Schutz, J.; Herdtweck, E.; Herrmann, W. A. Organometallics 2005, 24, 4416–4426;
(d) Stylianides, N.; Danopoulos, A. A.; Pugh, D.; Hancock, F.; Zanotti-Gerosa, A.
Organometallics 2007, 26, 5627–5635; (e) Liu, Z.; Zhang, T.; Shi, M.
Organometallics 2008, 27, 2668–2671.
3
7
00 MHz, TMS): d 5.84 (1H, s, CH), 6.64 (2H, d, J = 2.1 Hz, @CH),
.01 (2H, t, J = 7.8 Hz, Ar), 7.15–7.22 (4H, m, Ar), 7.35–7.40 (6H,
m, Ar), 7.93 (2H, s, NH).
7.
For some reviews: (a) Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C. P. J.
Organomet. Chem. 1999, 576, 23–41; (b) Bedford, R. B. Chem. Commun. 2003,
Acknowledgements
1
787–1796; (c) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759–
We thank the Shanghai Municipal Committee of Science and
Technology (06XD14005 and 08dj1400100-2), National Basic Re-
search Program of China (973)-2009CB825300 and the National
Natural Science Foundation of China for financial support
1792; (d) Farina, V. Adv. Synth. Catal. 2004, 346, 1553–1582; (e) Beletskaya, I. P.;
Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055–4082; (f) Dupont, J.;
Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527–2572; Some examples of
palladacycles in Heck reaction and coupling reactions: (a) Ohff, M.; Ohff, A.; van
der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687–11688; (b)
Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361–1362; (c) Ohff,
M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357–358; (d) Gruber, A. S.; Zim,
D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287–1290; (e) Wu,
Y. J.; Hou, J. J.; Yun, H. Y.; Cui, X. L.; Yuan, R. J. J. Organomet. Chem. 2001, 639,
(
20872162, 20672127 and 20732008).
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