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Bielawski, Christopher W.
Synthetic Materials & Macromolecules
Research Interests
  • Synthetic chemistry, materials science, polymer chemistry, catalysis, carbon-based materials

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Diamidocarbenes as versatile and reversible [2+1] cycloaddition reagents

Cited 42 times inthomson ciCited 41 times inthomson ci
Title
Diamidocarbenes as versatile and reversible [2+1] cycloaddition reagents
Author
Moerdyk, Jonathan P.Bielawski, Christopher W.
Keywords
N-HETEROCYCLIC CARBENE; CYCLOPROPANATION REACTIONS; ASYMMETRIC CYCLOPROPANATION; NUCLEOPHILIC CARBENE; STABLE CARBENE; ALKENES; PHOSPHINO(SILYL)CARBENES; N,N'-DIAMIDOCARBENE; STEREOSPECIFICITY; REACTIVITY
Issue Date
201204
Publisher
NATURE PUBLISHING GROUP
Citation
NATURE CHEMISTRY, v.4, no.4, pp.275 - 280
Abstract
We describe the synthesis of a variety of cyclopropanes and epoxides by combining a readily accessible and isolable N,N-2-diamidocarbene with a range of structurally and electronically diverse olefins and aldehydes, including electron-rich derivatives. Surprisingly, the cyclopropanation and epoxidation reactions were discovered to be rapid and thermally reversible at relatively low temperatures, two features often desired for applications that utilize dynamic covalent chemistry. In addition, a diamidocyclopropane derivative prepared via this method was hydrolysed successfully to form the corresponding linear carboxylic acid in a metal-and carbon monoxide-free hydrocarboxylation reaction. As such, diamidocarbenes are expected to find utility in the synthesis of cyclopropanes, epoxides and their derivatives, as well as in dynamic covalent chemistry applications.
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DOI
http://dx.doi.org/10.1038/nchem.1267
ISSN
1755-4330
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