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Synthesis 2014; 46(01): 35-41
DOI: 10.1055/s-0033-1338523
DOI: 10.1055/s-0033-1338523
practical synthetic procedures
Regioselective Direct C–H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process
Further Information
Publication History
Received: 29 July 2013
Accepted: 03 August 2013
Publication Date:
17 September 2013 (online)
Abstract
Nitrogen-containing heterocycles, including 1H-indoles and electron-deficient 1H-pyrroles, undergo a palladium/norbornene-cocatalyzed regioselective alkylation at the C–H bond adjacent to the NH group. A primary alkyl halide is used as the electrophile and the reaction proceeds smoothly under mild conditions to give 2-alkyl-1H-indoles and 2-substituted or 2,3-disubstituted 5-alkyl-1H-pyrroles in good yields.
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For reviews, see:
The direct C2 functionalization of indole can be achieved through C2-lithiation of N-protected indoles. For examples, see:
For selected recent examples of direct alkylation of pyrroles, see:
For reviews, see:
For selected examples, see: