2-Iodoaniline reacts with ketones in dioxane under reflux in the presence of a catalytic amount of Pd(dba)2/1, 1′-bis(di-iso-propylphosphino)ferrocene along with NaOtBu to afford 2-substituted indoles regioselectively in moderate to good yield.
FoxJ.M., HuangX., ChieffiA., and BuchwaldS. L., J. Am. Chem. Soc., 2000, 122, 1360 and references cited therein.
2.
MuratakeH., HayakawaA., and NatsumeM., Tetrahedron Lett., 1997, 38, 7577; H. Muratake and M. Natsume, Tetrahedron Lett., 1997, 38, 7581.
3.
PaluckiM., and BuchwaldS. L., J. Am. Chem. Soc., 1997, 119, 11108.
4.
HamannB.C., and HartwigJ. F., J. Am. Chem. Soc., 1997, 119, 12382.
5.
TeraoY., SatohT., MiuraM., and NomuraM., Tetrahedron Lett., 2000, 56, 1315.
6.
For the synthesis of indoles from 2-halo nitroarenes and ketones by initial palladium-catalysed α-arylation and subsequent electrophile induction and reductive cyclisation: RutherfordJ.L., RainkaM. P., and BuchwaldS. L., J. Am. Chem. Soc., 2002, 124, 15168; For the synthesis of indoles from 2-iodoaniline and cyclic ketones under Pd(OAc)2/DABCO: C. Chen, D.R. Lieberman, R.D. Larsen, T.R. Verhoeven and P.J. Reider, J. Org. Chem., 1997, 62, 2676.
7.
Our recent series on ruthenium-catalysed synthesis of indoles: ChoC.S., LimH. K., ShimS. C., KimT.-J., and ChoiH.-J., Chem. Commun., 1998, 995; C.S. Cho, J.H. Kim and S.C. Shim, Tetrahedron Lett., 2000, 41, 1811; C.S. Cho, J.H. Kim, T.-J. Kim and S.C. Shim, Tetrahedron, 2001, 57, 3321; C.S. Cho, J.H. Kim, H.-J. Choi, T.-J. Kim and S.C. Shim, Tetrahedron Lett., 2003, 44, 2975.
8.
KawatsuraM., and HartwigJ. F., J. Am. Chem. Soc., 1999, 121, 1473.
9.
RettigM.F., and MaitlisP. M., Inorg. Synth., 1992, 28, 110.
10.
AdamG., AndrieuxJ., and PlatM., Tetrahedron, 1985, 41, 399.
11.
KabalkaG.W., WangL., and PagniR. M., Tetrahedron, 2001, 57, 8017.
12.
SlättJ., and BergmanJ., Tetrahedron, 2002, 58, 9187.
13.
BourdaisJ., and LorreA., Eur. J. Med. Chem., 1974, 9, 269.
