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Org Lett. 2004 Aug 19;6(17):2897-900.

Direct C-H bond arylation: selective palladium-catalyzed C2-arylation of N-substituted indoles.

Author information

1
Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, USA.

Abstract

We present a new, practical method by which N-substituted indoles may be selectively arylated in the C2-position with good yields, low catalyst loadings, and a high degree of functional group tolerance. Our investigation found that two competitive processes, namely, the desired cross-coupling and biphenyl formation, were operative in this reaction. A simple kinetic model was formulated that proved to be instructive and provided useful guidelines for reaction optimization; the approach described within may prove to be useful in other catalytic cross-coupling processes.

PMID:
15330642
DOI:
10.1021/ol0490072

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