Acid directed in situ oxidation and decarboxylation of 4,4′,6,6′-tetra-methyl-2,2′-bipyridine: Synthesis and structural characterisation of 4,4′,6-tri-carboxy-2,2′-bipyridine and its copper(II) coordination polymer

Kelly, Niamh R.; Goetz, Sandrine; Hawes, Chris S.; Kruger, Paul E.

doi:10.1016/j.ica.2012.12.033

Inorganica Chimica Acta

2013

DOI: 10.1016/j.ica.2012.12.033

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Acid directed in situ oxidation and decarboxylation of 4,4′,6,6′-tetra-methyl-2,2′-bipyridine: Synthesis and structural characterisation of 4,4′,6-tri-carboxy-2,2′-bipyridine and its copper(II) coordination polymer

Niamh R. Kelly

Sandrine Goetz

Chris S. Hawes

et al.

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Cited by 11 publications

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“…It is noteworthy that the Krapcho demethoxycarbonylation is usually performed in a polar aprotic solvent . For non‐exhaustive examples of Cu 2+ decarboxylation, see, for some examples where Cu + is involved, see …”

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A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

Chapuis

Richard

2018

Helvetica Chimica Acta

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Dehydrohedione (DHH) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a, by treatment with CuBr2, in MeOH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX2 Kochi's conditions goes preferentially through the pathway involving intermediates 2b/2c and 7a, rather than 3a/3b or 8a/8b, essentially via α‐halogenation/dehydrohalogenation of the ketone moiety, both mediated by CuX2, while in‐situ decarbomethoxylation is promoted by the resulting CuX in refluxing MeOH.

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confidence: 99%

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

Chapuis

Richard

2018

Helvetica Chimica Acta

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Manganese(II) and cobalt(II) complexes based on pyridyl diimide: in situ ligand formation, crystal structures, and sorption properties

Cheng

Pan

et al. 2016

Transit Met Chem

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A novel iron(III) complex: synthesis, spectra, X-ray structure photoluminescence study, and antibacterial properties

2019

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Acid directed in situ oxidation and decarboxylation of 4,4′,6,6′-tetra-methyl-2,2′-bipyridine: Synthesis and structural characterisation of 4,4′,6-tri-carboxy-2,2′-bipyridine and its copper(II) coordination polymer

Cited by 11 publications

References 41 publications

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

Manganese(II) and cobalt(II) complexes based on pyridyl diimide: in situ ligand formation, crystal structures, and sorption properties

A novel iron(III) complex: synthesis, spectra, X-ray structure photoluminescence study, and antibacterial properties

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Acid directed in situ oxidation and decarboxylation of 4,4′,6,6′-tetra-methyl-2,2′-bipyridine: Synthesis and structural characterisation of 4,4′,6-tri-carboxy-2,2′-bipyridine and its copper(II) coordination polymer

Cited by 11 publications

References 41 publications

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione® Precursor

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione® Precursor

Manganese(II) and cobalt(II) complexes based on pyridyl diimide: in situ ligand formation, crystal structures, and sorption properties

A novel iron(III) complex: synthesis, spectra, X-ray structure photoluminescence study, and antibacterial properties

Contact Info

Product

Resources

About

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor