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J Org Chem. 2007 Feb 16;72(4):1476-9.

Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

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

Abstract

This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

PMID:
17288392
[PubMed - indexed for MEDLINE]
PMCID:
PMC2971669
Free PMC Article
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