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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Remarkably reactive dihydroindoloindoles via palladium-catalysed dearomatisation
Robin B Bedford1, Natalie Fey, Mairi F Haddow
1School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. r.bedford@bristol.ac.uk
Palladium catalysis enables the synthesis of novel 5,10b-dihydroindolo[2,3-b]indoles. These unique indoloindole heterocycles readily react with various nucleophiles, showcasing their high reactivity.
Area of Science:
- Organic Chemistry
- Heterocyclic Chemistry
- Catalysis
Background:
- Indolo[2,3-b]indoles represent a unique heterocyclic scaffold.
- Palladium-catalyzed reactions are crucial for novel molecule synthesis.
- Dearomatisation offers a pathway to complex structures.
Purpose of the Study:
- To synthesize a novel class of indoloindole heterocycles.
- To explore palladium-catalyzed dearomatisation reactions.
- To investigate the reactivity of the newly formed compounds.
Main Methods:
- Palladium-catalyzed dearomatisation reactions.
- Synthesis of 5,10b-dihydroindolo[2,3-b]indoles.
- Reactions with water and organometallic nucleophiles (hydride, alkyl, aryl, allyl).
Main Results:
- Access to a previously unknown class of 5,10b-dihydroindolo[2,3-b]indoles.
- Demonstration of facile reactions with water.
- Observation of high reactivity with various organometallic nucleophiles.
Conclusions:
- Palladium-catalyzed dearomatisation provides a novel route to indoloindoles.
- The synthesized 5,10b-dihydroindolo[2,3-b]indoles are highly reactive.
- These compounds serve as versatile building blocks for further chemical transformations.
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