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Three-Component Synthesis of N-Boc-4-iodopyrroles and Sequential One-Pot Alkynylation

Eugen Merkul, Christina Boersch, Walter Frank and Thomas J. J. Müller*

*Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany, Email: thomasjj.muelleruni-duesseldorf.de

E. Merkul, C. Boersch, W. Frank, T. J. J. Müller, Org. Lett., 2009, 11, 2269-2272.

DOI: 10.1021/ol900581a (free Supporting Information)


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Abstract

(Hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides can be efficiently coupled with N-Boc-protected propargylamine to produce ynones which are converted to 2-substituted N-Boc-4-iodopyrroles in a one-pot reaction. Upon addition of a further alkyne, another Sonogashira coupling can be carried out in a one-pot fashion.

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Key Words

Pyrroles, Iodination, Sonogashira Coupling


ID: J54-Y2009-1630