7
, 5063; (d) Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857; (e) Ke, B.; Qin, Y.; He,
Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751; (f) Gu, D.; Ji, S.-J.; Jiang, Z.-Q.; Zhou,
M.-F.; Loh, T.-P. Synlett 2005, 959; (g) Wang, L.; Han, J.; Tian, H.; Sheng, J.; Fan, Z.; Tang, X.
SynLett 2005, 337; (h) Shi, M.; Cui, S.-C.; Li, Q.-J. Tetrahedron 2004, 60, 6679; (i) Nagarajan, R.;
Perumal, P. T. Tetrahedron 2002, 58, 1229; (j) Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S. R.;
Kumar, G. M.; Madan, C. Synthesis 2001, 783; (k) Chen, D.; Yu, L.; Wang, G. Tetrahedron Lett.
1
996, 37, 4467.
4
.
For recent examples of transition metal-catalyzed reactions, see: (a) Xia, D.; Wang, Y.; Du, Z.;
Zheng, Q.-Y.; Wang, C. Org. Lett. 2012, 14, 588; (b) Young, P. C.; Hadfield, M. S.; Arrowsmith,
L.; Macleod, K. M.; Mudd, R. J.; Jordan-Hore, J. A.; Lee, A.-L. Org. Lett. 2012, 14, 898; (c)
Munoz, M. P.; Torre, M. C.; Sierra, M. A. V. Chem. Eur. J. 2012, 18, 4499; (d) Barluenga, J.;
Fernandez, A.; Rodriguez, F.; Fananas, F. J. J. Organomet. Chem. 2009, 694, 546; (e). Nair, V.;
Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857.
5
. A few examples of bisindolylation reaction under solvent-free condition, see: (a) Chakrabarty, M.;
Mukherjee, R.; Mukherji, A.; Arima, S.; Harigaya, Y. Heterocycles 2006, 68, 1659; (b) Pore, D.
M.; Desai, U. V.; Thopate, T. S.; Wadgaonkar, P. P. ARKIVOC 2006, 75; (c) Ji, S.-J.; Wang,
S.-Y.; Zhang, Y.; Loh, T.-P. Tetrahedron 2004, 60, 2051; (d) Chakrabarty, M.; Basak, R.; Ghosh,
N.; Harigaya, Y. Tetrahedron 2004, 60, 1941; (e) Bartoli, G.; Bosco, M.; Foglia, G.; Giuliani, A.;
Marcantoni, E.; Sambri, L. Synthesis 2004, 895.
6
.
(a) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Second
Edition. Wiley-VCH GmbH & Co. KGaA. 2013; (b) Uneyama, K. Organofluorine Chemistry
Wiley-Blackwell: Oxford, 2006.
7
8
.
.
(a) Xing, C.; Li, X.; Zhu, S.; Zhao, J.; Zhu, S. Tetrahedron Lett. 2006, 47, 4951; (b) Xing, C.; Zhu,
S. J. Org. Chem. 2004, 69, 6486.
(a) Sasaki, S.; Ikekame, Y.; Tanayama, M. Yamauchi, T.; Higashiyama, K. SynLett 2012, 23,
2
2
699. (b) Nie, J.; Zhang, G.-W.; Wang, L.; Fu, A.; Zheng, Y.; Ma, J.-A. Chem. Commun. 2009,
356.
9
1
.
(a) Gong, Y.; Kato, K. J. Fluorine Chem. 2002, 116, 103. (b) Gong, Y.; Kato, K. J. Fluorine
Chem. 2001, 108, 83.
0
Trifluoromethyl cyclopropyl ketone 1a was prepared with a revised procedure based on the
method reported by Shreeve et al. (Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org.
Chem. 1999, 64, 2873.) 1a was obtained as a mixture which contains ~35 mol% of
bis(trimethylsilyl)ether. The existence of bis(trimethylsilyl)ether might have a weak influence on
the bisindolylation reaction. See surporting information for details.
7