Copper-mediated multiple C-H functionalization of aromatic N-heterocycles: Bromoamination of indoles and pyrroles

Alex John; Kenneth M. Nicholas

doi:10.1021/om300553b

Copper-mediated multiple C-H functionalization of aromatic N-heterocycles: Bromoamination of indoles and pyrroles

Alex John, Kenneth M. Nicholas

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

Abstract

A copper-mediated bromoamination of aromatic N-heterocycles has been achieved using oxime esters as the N-reagents under mild conditions (ca. 70 °C). The reaction with N-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the bromoaminated product, 3aa-Br. With N-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method.

Original language	English (US)
Pages (from-to)	7914-7920
Number of pages	7
Journal	Organometallics
Volume	31
Issue number	22
DOIs	https://doi.org/10.1021/om300553b
State	Published - Nov 26 2012

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abstract = "A copper-mediated bromoamination of aromatic N-heterocycles has been achieved using oxime esters as the N-reagents under mild conditions (ca. 70 °C). The reaction with N-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the bromoaminated product, 3aa-Br. With N-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method.",

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AU - Nicholas, Kenneth M.

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N2 - A copper-mediated bromoamination of aromatic N-heterocycles has been achieved using oxime esters as the N-reagents under mild conditions (ca. 70 °C). The reaction with N-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the bromoaminated product, 3aa-Br. With N-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method.

AB - A copper-mediated bromoamination of aromatic N-heterocycles has been achieved using oxime esters as the N-reagents under mild conditions (ca. 70 °C). The reaction with N-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the bromoaminated product, 3aa-Br. With N-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method.

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Copper-mediated multiple C-H functionalization of aromatic N-heterocycles: Bromoamination of indoles and pyrroles

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