The structures and reactivity of NHC-supported copper(<scp>i</scp>) triphenylgermyls

Charman, Rex S. C.; Evans, Nick J.; English, Laura E.; Neale, Samuel E.; Vasko, Petra; Mahon, Mary F.; Liptrot, David J.

doi:10.1039/d3sc05862j

Chem. Sci.

2024

DOI: 10.1039/d3sc05862j

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The structures and reactivity of NHC-supported copper(i) triphenylgermyls

Rex S. C. Charman,

Nick J. Evans,

Laura E. English

et al.

Abstract: Four N-heterocyclic carbene (NHC) supported copper(i) germyls have been synthesised containing both normal- and ring-expanded NHCs. Their π-insertion and σ-bond metathesis chemistry has been explored in stoichiometric and catalytic regimes.

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Cited by 6 publications

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“…5 Moreover, the ring-expanded NHC (RE-NHC) 6-Dipp has been found to be a privileged motif in isolating and structurally characterising a wide range of interesting copper complexes. Routes to these generally start from (6-Dipp)CuO t Bu and have provided access to an isolable NHC-copper hydride dimer, 6 a range of highly stable NHC-copper boryls, 7–9 as well as a copper formimidoyl, 10 copper phosphide, 11 copper stannyl, 12 and copper germyl, 13 amongst others.…”

mentioning

confidence: 99%

Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper complexes

Babula,

Charman,

Hobson

et al. 2024

Dalton Trans.

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confidence: 99%

Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper complexes

Babula,

Charman,

Hobson

et al. 2024

Dalton Trans.

Self Cite

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Nucleophilic Triphenylgermanides of Magnesium and Calcium

Kennedy,

Pearce,

Morris

et al. 2024

Chemistry A European J

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The dimeric calcium and magnesium hydrides, [(BDI)AeH]2 [BDI = HC{(Me)CNDipp}2, Dipp = 2,6‐i‐Pr2C6H3; Ae = Mg or Ca] do not react with Ph3GeH in non‐coordinating solvent. Addition of THF, however, induces deprotonation and access to monomeric Ae‐germanide complexes, [(BDI)Ae{GePh3}(THF)], both of which have been structurally characterized. Although this process is facile when Ae = Ca, the analogous magnesium‐based reaction requires heating to temperatures >100 °C, under which conditions germanide formation is complicated by THF ring opening and the generation of an alkaline earth germyl‐C‐terminated n‐butoxide, [(BDI)|Mg{μ2‐O(CH2)4GePh3}]. Reactions of [(BDI)Ca{GePh3}(THF)] with N,N'‐di‐isopropylcarbodiimide and benzophenone provide the respective germylamidinate and germylalkoxide derivatives, [(BDI)Ca{(i‐PrN)2CGePh3}(THF)] and [(BDI)Ca{OC(GePh3)Ph2}(THF)], demonstrating its potential as a well‐defined and soluble source of the [Ph3Ge]− anion in nucleophilic addition reactions.

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Synthesis, Structures, and Reactivity of Organostannanides and Organogermanides of Copper(I)

Charman,

Liptrot

2024

ChemPlusChem

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Organogermane and organostannane compounds are valuable reagents in cross coupling reactions, and copper(I) germanide and stannanide complexes can provide convenient access to these compounds. This review presents the chemistry of copper(I) germanide and stannanide complexes, with a particular focus on systems at the frontier of organic and inorganic chemistry where structural characterisation of coordination complexes facilitates rationalisation of organic mechanisms. These species show both similarities to, and significant divergences from their lighter silanide congeners. For example, they are all viable sources of the relevant organotetranide anion, but in the cases of both germanium and tin, the tetranides can be accessed via direct deprotonation of the corresponding tetranes, a reaction unknown for silicon. Further divergences between copper(I) germanides and stannanides are highlighted; whilst both can be used in productive organic transformations to access organotetranes, catalytic reactions are only reported for germanium. The rather striking ability of triphenlstannides to acts as sources of the phenyl anion are discussed; the mechanism of this reaction is still subject to discussion, but its absence in the chemistry of germanium and silicon is now well‐rationalised. We conclude this review by considering potential research directions in the synthesis and exploitation of copper(I) germanides and stannanides.

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The structures and reactivity of NHC-supported copper(i) triphenylgermyls

Abstract: Four N-heterocyclic carbene (NHC) supported copper(i) germyls have been synthesised containing both normal- and ring-expanded NHCs. Their π-insertion and σ-bond metathesis chemistry has been explored in stoichiometric and catalytic regimes.

Cited by 6 publications

References 32 publications

Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper complexes

Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper complexes

Nucleophilic Triphenylgermanides of Magnesium and Calcium

Synthesis, Structures, and Reactivity of Organostannanides and Organogermanides of Copper(I)

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