Base Metal Catalyzed Isocyanide Insertions.
Jurriën W Collet1,2, Thomas R Roose1, Eelco Ruijter1
1Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ, Amsterdam, The Netherlands.
Angewandte Chemie (International Ed. in English)
|July 10, 2019
Summary
This review highlights base metal-catalyzed reactions using isocyanides, which are versatile C1 building blocks. These reactions offer sustainable alternatives to precious metal catalysis in organic synthesis.
Area of Science:
- Organometallic Chemistry
- Synthetic Organic Chemistry
- Catalysis
Background:
- Isocyanides are versatile C1 building blocks reactive towards nucleophiles, electrophiles, and radicals.
- They are valuable inputs for multicomponent reactions (MCRs) and cascade processes.
- In organometallic chemistry, isocyanides act as ligands, modifying reactivity through metal coordination.
Purpose of the Study:
- To review emerging base metal-catalyzed reactions involving isocyanides.
- To highlight the potential of these reactions in synthetic organic chemistry.
- To discuss proposed catalytic cycles and categorize literature based on metal-ligand interactions.
Main Methods:
- Literature review focusing on base metal catalysis with isocyanides.
- Categorization of reactions based on the heteroatom bound to the metal and the type of bonding.
- Discussion of proposed catalytic cycles for base metal-mediated isocyanide transformations.
Main Results:
- Palladium-catalyzed isocyanide insertion reactions are well-established but precious metal-dependent.
- Reports on earth-abundant base metal catalysis for isocyanide transformations are scarce but growing.
- This review consolidates and analyzes the existing literature on base metal catalyzed isocyanide chemistry.
Conclusions:
- Base metal catalysis offers a sustainable and cost-effective alternative for isocyanide-based synthetic transformations.
- Further research into mechanistic studies is needed to fully understand and optimize these reactions.
- Expanding base metal catalysis for isocyanides holds significant promise for green synthetic organic chemistry.
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