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200517.fm Page 130 Friday, March 18, 2005 2:52 PM
2005
Indole derivatives
R 0140
A Facile Regiocontrol in the Palladium-Catalyzed Annulation of Fluorine-ConInternal Alkynes with Variously Substituted 2-Iodoanilines: A New
17- 118 taining
Regioselective Synthesis of 2- or 3-Fluoroalkylated Indole Derivatives. — It is
found that the nature of the ligand strongly affects the regioselective outcome of the
title annulation. PPh3 favors the formation of 2-fluoroalkylated indoles, whereas in the
presence of P(o-tolyl)3, 3-fluoroalkylated indoles are mainly obtained. Interestingly, the
coupling of alkynes bearing a benzylic moiety leads to trifluoroethylated indoles instead of trifluoromethylated products indicating formation of allene intermediates. —
(KONNO*, T.; CHAE, J.; ISHIHARA, T.; YAMANAKA, H.; J. Org. Chem. 69
(2004) 24, 8258-8265; Dep. Chem. Mater. Technol., Kyoto Inst. Technol., Sakyo,
Kyoto 606, Japan; Eng.) — Jannicke
200517.fm Page 131 Friday, March 18, 2005 2:52 PM
2005
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