Copper, silver and gold-based catalysts for carbene addition or insertion reactions

Díaz‐Requejo, M. Mar; Pérez, Pedro J.

doi:10.1016/j.jorganchem.2005.07.092

Cited by 112 publications

(61 citation statements)

References 28 publications

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“…Recently, there was a report of NHC silver complexes catalyzing a carbene transfer reaction from ethyl diazoacetate to cyclohexane. [27] On another occasion, Waymouth and Hedrick reported NHC silver complexes as novel carbene delivery agents for ring-opening polymerization of -lactides and for transesterification reactions. [28] These promising applications of NHC silver complexes in chemical catalysis have opened up a new frontier of research.…”

Section: Resultsmentioning

confidence: 99%

“…[26] Interestingly, apart from its exclusive use in transmetallation reactions, a few reports of the utility of NHC silver complexes in chemical catalysis have appeared lately. For instance, there have been reports of the NHC silver complexes exhibiting catalytic activity in ethyl diazoacetate (EDA) assisted carbene transfer reactions, [27] in transesterification reactions, and in ring-opening lactide polymerization reactions. [28] Thus, for the NHC silver complexes, the focus of research is gradually shifting from being solely used in transmetallation reactions to its applications in chemical catalysis, which has opened up a new frontier of research.…”

Section: Introductionmentioning

confidence: 99%

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A Cationic (N‐Heterocyclic carbene)silver Complex as Catalyst for Bulk Ring‐Opening Polymerization ofL‐Lactides

et al. 2006

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Synthetic, theoretical, and catalysis studies of a cationic functionalized N-heterocyclic carbene complex of silver, namely, is reported. Specifically, 1b was synthesized by the reaction of 1-isopropyl-3-(N-phenylacetamido)imidazolium chloride (1a) with Ag 2 O in 64 % yield; 1a was synthesized by the alkylation reaction of 1-isopropylimidazole with N-phenyl chloroacetamide in 90 % yield. The molecular structure of 1b was determined by X-ray diffraction studies and was found to be active for polymerization of L-lactide at elevated temperatures under solvent-free melt conditions to give polylactide of moderate molecular weight with narrow molecular weight distribution. Density functional theory studies of the cationic species 2b, derived from NHC silver complex 1b, were employed to obtain an understanding of the structure, bonding, and electronic features of the mole-

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Cationic (N‐Heterocyclic carbene)silver Complex as Catalyst for Bulk Ring‐Opening Polymerization ofL‐Lactides

et al. 2006

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“…Although the dirhodium catalysts are the most commonly used today, other metals are still being explored for carbenoid C-H insertion [35]. These include copper [36][37][38][39][40][41][42][43][44][45], silver [46,47], iron [48][49][50], gold [40], and magnesium [51,52], and most will be discussed in context, particularly in Sect.…”

Section: Fig 3 Chiral Dirhodium Catalysts Discussed In This Chaptermentioning

confidence: 99%

Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

Davies

Dick

2009

C-H Activation

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The functionalization of carbon-hydrogen bonds through transition metal carbenoid insertion is becoming a powerful method for the construction of new carbon-carbon bonds in organic synthesis. This chapter will highlight recent developments in this field, while placing it within its historical context. Intramolecular carbenoid C-H insertion will be covered first, focusing on formation of three-and six-membered rings, as well as the use of nontraditional substrates. Additionally, the most recent progress in asymmetric catalysis will be discussed. The bulk of the chapter will concentrate on intermolecular transformations, emphasizing both the effect of substrate structure and the influence of carbene substituent electronics on the regioselectivity of the reactions. Vinyldiazoacetates will be covered as a distinct class of carbenoid precursors, as they have been shown to initiate a variety of unique transformations, such as the combined C-H activation/Cope rearrangement. Finally, the synthetic utility of carbenoid C-H insertion reactions, both intra-and intermolecular, will be displayed through their use in the total syntheses of a number of natural products and pharmaceuticals.

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“…Pyrazolylborate auxiliary ligands have played an important role in several key areas of coinage metal (Cu, Ag, Au) chemistry [1][2][3][4][5] and they have also proved immensely useful for the stabilization of group 11 metal complexes of small carbon-based ligands, [6,7] the synthesis of metalloenzyme models relevant to biochemistry, [8][9][10][11] the development of homogeneous catalysts [12][13][14][15][16] and in the MOCVD of copper films. [17] An area of particular interest to us has been the effects of electron-withdrawing substituents on scorpionates and their metal adducts.…”

Section: Introductionmentioning

confidence: 99%

Copper(I) Isocyanide and Phosphane Complexes of Fluorinated Mono‐ and Bis(pyrazolyl)borates

et al. 2009

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Copper, silver and gold-based catalysts for carbene addition or insertion reactions

Cited by 112 publications

References 28 publications

A Cationic (N‐Heterocyclic carbene)silver Complex as Catalyst for Bulk Ring‐Opening Polymerization ofL‐Lactides

A Cationic (N‐Heterocyclic carbene)silver Complex as Catalyst for Bulk Ring‐Opening Polymerization ofL‐Lactides

Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

Copper(I) Isocyanide and Phosphane Complexes of Fluorinated Mono‐ and Bis(pyrazolyl)borates

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