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Communication | Special issue | Vol 80, No. 2, 2010, pp.895-901
Published online, 13th October, 2009
DOI: 10.3987/COM-09-S(S)117
Observation of 2,7-Disubstitution in Palladium Catalysed Directed C-H Activation of Indoles

Guilia Fanton, Nicola M. Coles, Andrew R. Cowley, Jonathan P. Flemming, and John M. Brown*

*Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.

Abstract

In previous work, controlled C-H activation and catalytic Heck reaction at the 2-position of indole was demonstrated. This was achieved by means of a N-(2-pyridylmethyl) directing group. In the course of extending the initial observations it was discovered that the corresponding N-(1-isoquinolylmethyl)indole derivative was prone to a further oxidative Heck reaction giving rise to a 2,7-disubstituted product, which was characterised by NMR and X-ray analysis. The parent pyridine showed no tendency for a second substitution reaction at the indole 7-position, but the related N-(2-quinolylmethyl) derivative did. In the case of the corresponding 6-methylphenanthridinyl derivative, a novel oxidative C-C cleavage reaction was observed.