2015
DOI: 10.1002/anie.201507921
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Expanding the Ligand Framework Diversity of Carbodicarbenes and Direct Detection of Boron Activation in the Methylation of Amines with CO2

Abstract: A simple and convergent synthetic strategy used to increase the diversity of the carbodicarbene ligand framework through incorporation of unsymmetrical pendant groups is reported. Structural analysis and spectroscopic studies of ligands and their Rh complexes are reported. Reactivity studies reveal carbodicarbenes as competent organocatalysts for amine methylation using CO2 as a synthon. A unique BH-activated boron-carbodicarbene complex was isolated as a reaction intermediate, providing mechanistic insight i… Show more

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Cited by 166 publications
(98 citation statements)
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“…The bent structure of 4NHC bestows some unique features on this cumulene. Contrary to classical allenes, the bent allene, 2NHC , has two lone pairs on the same carbon that can form covalent bonds with some metals . Therefore, it is expected that the bent 4NHC will have some similar features that distinguish it from the rest of the [4]cumulenes.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The bent structure of 4NHC bestows some unique features on this cumulene. Contrary to classical allenes, the bent allene, 2NHC , has two lone pairs on the same carbon that can form covalent bonds with some metals . Therefore, it is expected that the bent 4NHC will have some similar features that distinguish it from the rest of the [4]cumulenes.…”
Section: Resultsmentioning
confidence: 99%
“…Special attention has been paid to carbones that have carbenes as ligands, because they can be described as bent allenes. These types of allenes are interesting because, as opposed to linear allenes, they have two lone pairs that could coordinate to a metal center . Carbones have been expanded to include other main‐group atoms, such as nitrogen, boron, silicon, and germanium (EL 2 ) .…”
Section: Introductionmentioning
confidence: 99%
“…In order to broaden the scope of the CDC ligand framework, Ong and Chen searched for another alternative paradigm to assemble CDCs bearing unsymmetrical units toward increasing the diversity of this chemistry . This simple choice of an unsymmetrical framework could be achieved by a simple S N 2 reaction of nucleophilic and electrophilic synthons.…”
Section: Unsymmetrical Carbodicarbenesmentioning
confidence: 99%
“…[1,2] Electron-precise diboranes(4) can be regarded as boryl-substituted trigonal boranes, as was demonstrated by the fact that quaternization of one borona tom of diboranes(4) with either an eutral or anionic base can provide practical "boryl anion"s urrogates in organic synthesis. [1,2] Electron-precise diboranes(4) can be regarded as boryl-substituted trigonal boranes, as was demonstrated by the fact that quaternization of one borona tom of diboranes(4) with either an eutral or anionic base can provide practical "boryl anion"s urrogates in organic synthesis.…”
mentioning
confidence: 99%