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Michlik, Stefan ; Kempe, Rhett:
A sustainable catalytic pyrrole synthesis.
In: Nature Chemistry.
Bd. 5
(2013)
Heft 2
.
- S. 140-144.
ISSN 1755-4349
DOI: https://doi.org/10.1038/nchem.1547
Abstract
The pyrrole heterocycle is a prominent chemical motif and is found widely in natural products, drugs, catalysts and advanced materials. Here we introduce a sustainable iridium-catalysed pyrrole synthesis in which secondary alcohols and amino alcohols are deoxygenated and linked selectively via the formation of C-N and C-C bonds. Two equivalents of hydrogen gas are eliminated in the course of the reaction, and alcohols based entirely on renewable resources can be used as starting materials. The catalytic synthesis protocol tolerates a large variety of functional groups, which includes olefins, chlorides, bromides, organometallic moieties, amines and hydroxyl groups. We have developed a catalyst that operates efficiently under mild conditions.