Journal ArticleDOI
A Facile Route to Functionalized N-Heterocyclic Carbenes (NHCs) with NHC Base-Stabilized Dichlorosilylene
TLDR
Silyl-substituted NHC 2 reacts easily with 1-azidoadamantane to form triazene 3, in which the exocyclic C=N bond is slightly shorter than those of regular NHC-derived triazines.Abstract:
Reaction of IPr x SiCl(2) (1) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] with 1-azidoadamantane leads to functionalized N-heterocyclic carbene (NHC) 2. Silyl-substituted NHC 2 reacts easily with 1-azidoadamantane to form triazene 3, in which the exocyclic C=N bond is slightly shorter than those of regular NHC-derived triazines. 2 could serve as a promising ligand for transition metals.read more
Citations
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Journal ArticleDOI
NHCs in Main Group Chemistry.
Vitaly Nesterov,Dominik Reiter,Prasenjit Bag,Philipp Frisch,Richard Holzner,Amelie Porzelt,Shigeyoshi Inoue +6 more
TL;DR: A general overview of the chemistry of low-coordinate main group element compounds, basic synthetic approaches, key features of NHC-main group element adducts, and might be useful for the broad research community are given.
Journal ArticleDOI
A Viable Anionic N-Heterocyclic Dicarbene
Yu-Zhong Wang,Yaoming Xie,Mariham Y. Abraham,Pingrong Wei,Henry F. Schaefer,Paul von Ragué Schleyer,Gregory H. Robinson +6 more
TL;DR: The first anionic N-heterocyclic dicarbene, polymeric, prepared by lithiation of the imidazole monocarbene by the formation of the group 13 Lewis acid adducts (THF)(2)Li.
Journal ArticleDOI
Dichlorosilylene: a high temperature transient species to an indispensable building block.
TL;DR: This Account describes the results using (NHC)SiCl(2) primarily from the laboratory, including findings by other researchers, and emphasizes the novel silicon compounds, which supposedly existed only as short-lived species.
Journal ArticleDOI
Anionic N-heterocyclic carbenes: Synthesis, coordination chemistry and applications in homogeneous catalysis
TL;DR: The chemistry and application of anionic N-Heterocyclic carbenes (NHCs) are summarized in this article by gathering all records about NHCs since their first appearance in 1996.
Journal ArticleDOI
Chemistry of functionalized silylenes
TL;DR: The functional group attached to the α-position of the silicon(II) centre plays a key role to determine the final product as mentioned in this paper. But the chemistry of functionalized silylenes is markedly different from the previously reported dicoordinate silybenes.
References
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N-heterocyclic carbenes: a new concept in organometallic catalysis.
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Heterocyclic Carbenes: Synthesis and Coordination Chemistry
TL;DR: New methods for the synthesis of complexes with N-heterocyclic carbene ligands such as the oxidative addition or the metal atom template controlled cyclized isocyanides have been developed recently.
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Organocatalysis by N-Heterocyclic Carbenes
TL;DR: The inversion of the classical reactivity (Umpolung) opens up new synthetic pathways in biochemical processes as nucleophilic acylations and in nature, the coenzyme thiamine (vitamin B1), a natural thiazolium salt, utilizes a catalytic variant of this concept in biochemical process as nucleophile acylation.
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N‐Heterocyclic Carbenes as Organocatalysts
TL;DR: This work highlights the ever-increasing number of reactions that can be promoted by N-heterocyclic carbenes and investigates the role of benzoin condensation in these reactions.