3
036
S.-S. Pi et al.
LETTER
C.-L.; Zhong, P.; Li, J.-H. Tetrahedron 2008, 64, 10670.
(d) Luo, P.-S.; Yu, M.; Tang, R.-Y.; Zhong, P.; Li, J.-H.
Tetrahedron Lett. 2009, 50, 1066. (e) Luo, P.-S.; Wang, F.;
Li, J.-H.; Tang, R.-Y.; Zhong, P. Synthesis 2009, 921.
(10) General Procedure for the Copper-Catalyzed Tandem
Reaction of 2-Haloanilimine Derivatives with
(
6) (a) Jordan, A. D.; Luo, C.; Retiz, A. B. J. Org. Chem. 2003,
8, 8693. (b) Mu, X.-J.; Zou, J.-P.; Zeng, R.-S.; Wu, J.-C.
6
Tetrahedron Lett. 2005, 46, 4345. (c) Bose, D. S.; Idrees,
M. J. Org. Chem. 2006, 71, 8261. (d) Bose, D. S.; Idrees,
M. Tetrahedron Lett. 2007, 48, 669. (e) Bose, D. S.; Idrees,
M.; Srikanth, B. Synthesis 2007, 819. (f) Downer-Riley,
N. K.; Jackson, Y. A. Tetrahedron 2008, 64, 7741.
Tetraalkylthiuram Disulfides
(
g) Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org.
A flame-dried Schlenk tube with a magnetic stirring bar was
charged with 2-haloanilimine derivative 1 (0.2 mmol),
tetraalkylthiuram disulfide (0.15 mmol), CuBr (1.4 mg, 0.01
mmol), Cs CO (196 mg, 0.6 mmol), and DMSO (1 mL).
Lett. 2008, 10, 5147. (h) Thiel, O. R.; Bernard, C.; King, T.;
Dilmeghani-Seran, M.; Bostick, T.; Larsen, R. D.; Faul,
M. M. J. Org. Chem. 2008, 73, 3508. (i) Pande, S.; Saha,
A.; Jana, S.; Sarkar, S.; Basu, M.; Pradhan, M.; Sinha, A. K.;
Saha, S.; Pal, A.; Pal, T. Org. Lett. 2009, 11, 2792.
2
3
The reaction mixture was stirred at 80 °C for the indicated
time (Tables 1 and 2) until complete consumption of starting
material as monitored by TLC and GC-MS analysis. After
the reaction was finished, the mixture was poured into
EtOAc, washed with brine (3 × 10 mL), and extracted with
EtOAc. The combined organic layers were dried over anhyd
Na SO and evaporated under vacuum. The residue was
(
(
7) (a) Benedi, C.; Bravo, F.; Uriz, P.; Fernandez, E.; Claver, C.;
Castillon, S. Tetrahedron Lett. 2003, 44, 6073. (b) Joyce,
L. L.; Evindar, G.; Batey, R. A. Chem. Commun. 2004, 446.
(
(
c) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
d) Vera, M. D.; Pelletier, J. C. J. Comb. Chem. 2007, 9,
2
4
5
(
69. (e) Itoh, T.; Mase, T. Org. Lett. 2007, 9, 3687.
f) Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587.
8) (a) Grunwell, J. R. J. Org. Chem. 1970, 35, 1500.
b) Priefer, R.; Lee, Y. J.; Barrios, F.; Wosnick, J. H.;
purified by flash column chromatography (hexane–EtOAc)
to afford the desired product.
N,N-Dimethy-6-(trifluoromethyl)benzo[d]thiazol-2-
amine (4)
(
1
Lebuis, A. M.; Farrell, P. G.; Harpp, D. N.; Sun, A.; Wu, S.;
Mp 98.5–101.1 °C(uncorrected). H NMR (300 MHz,
Snyder, J. P. J. Am. Chem. Soc. 2002, 124, 5626.
CDCl ): d = 7.84 (s, 1 H), 7.58 (d, J = 8.5 Hz, 1 H), 7.52 (d,
3
1
3
(c) Krasovskiy, A.; Gavryushin, A.; Knochel, P. Synlett
J = 8.5 Hz, 1 H), 3.22 (s, 6 H). C NMR (75 MHz, CDCl3):
2
005, 2691. (d) Krasovskiy, A.; Gavryushin, A.; Knochel, P.
d = 170.3, 155.8, 131.2, 124.6 (q, J = 269.9 Hz, 1 C),
C–F
Synlett 2006, 792. (e) Krasovskiy, A.; Malakhov, V.;
Gavryushin, A.; Knochel, P. Angew. Chem. Int. Ed. 2006,
123.4, 122.8 (d, J = 32.2 Hz, 1 C), 122.1, 118.0, 40.2. 19F
C–F
NMR (283 MHz, CDCl ): d = –60.79. IR (KBr): 2913, 1616,
3
–
1
45, 6040.
1573, 1337, 1145, 1099 cm . LRMS (EI, 70 eV): m/z (%) =
+
(
9) (a) Tang, R.-Y.; Zhong, P.; Lin, Q.-L. J. Fluor. Chem. 2006,
246 (93) [M ], 217 (100). ESI-HRMS: m/z calcd for
+
+
127, 948. (b) Tang, R.-Y.; Zhong, P.; Lin, Q.-L. Synthesis
C H F N S [M + H] : 247.0511; found: 247.0503.
10 10 3 2
2007, 85. (c) Wang, Z.-L.; Tang, R.-Y.; Luo, P.-S.; Deng,
Synlett 2009, No. 18, 3032–3036 © Thieme Stuttgart · New York