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Regioselective Direct C-H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process

Lei Jiao, Thorsten Bach*

*Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany, Email: thorsten.bachch.tum.de

L. Jiao, T. Bach, Synthesis, 2014, 46, 35-41.

DOI: 10.1055/s-0033-1338523 (free Supporting Information)


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Abstract

Nitrogen-containing heterocycles, including 1H-indoles and electron-deficient 1H-pyrroles, undergo a smoth and mild palladium/norbornene-cocatalyzed regioselective alkylation with primary alkyl bromides at the C-H bond adjacent to the NH group to give 2-alkyl-1H-indoles and 2-substituted or 2,3-disubstituted 5-alkyl-1H-pyrroles in good yields.

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proposed mechanism



Key Words

catalysis, alkylations, regioselectivity, heterocycles, palladium, indoles, pyrroles, indoles


ID: J66-Y2014