Addition of a Cyclophosphine to Nitriles: An Inorganic Click Reaction Featuring Protio, Organo, and Main‐Group Catalysis

The addition of a cyclotriphosphine to a broad range of nitriles gives access to the first examples of free 1‐aza‐2,3,4‐triphospholenes in a rapid, ambient temperature, one‐pot, high‐yield protocol. The reaction produces electron‐rich heterocycles (four lone pairs) and features homoatomic σ‐bond het...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-08, Vol.56 (32), p.9536-9540
Main Authors: Chitnis, Saurabh S., Sparkes, Hazel A., Annibale, Vincent T., Pridmore, Natalie E., Oliver, Alex M., Manners, Ian
Format: Article
Language:English
Subjects:
Ambient temperature
Azides (inorganic)
Catalysis
Chemical bonds
Chemical reactions
click chemistry
Cyanide
Cycloaddition
heterocycles
main-group elements
Nitriles
Organic compounds
phosphorus
Temperature effects
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Summary:The addition of a cyclotriphosphine to a broad range of nitriles gives access to the first examples of free 1‐aza‐2,3,4‐triphospholenes in a rapid, ambient temperature, one‐pot, high‐yield protocol. The reaction produces electron‐rich heterocycles (four lone pairs) and features homoatomic σ‐bond heterolysis, thereby combining the key features of the 1,3‐dipolar cycloaddition chemistry of azides and cyclopropanes. Also reported is the first catalytic addition of P−P bonds to the C≡N bond. The coordination chemistry of the new heterocycles is explored. Click for P: The catalytic cycloaddition of nitriles to a cyclotriphosphine gives the first examples of free 1‐aza‐2,3,4‐triphospholenes. This electrophile‐mediated reaction is rapid (
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201704991