Skipping the one C–X one C–C bond rule in Kumada cross coupling reaction. Diarylation from an only B–I in metallacarboranes

Arderiu, Víctor Sánchez; Viñas, Clara; Teixidor, Francesc

doi:10.1016/j.jorganchem.2015.06.003

Cited by 5 publications

(3 citation statements)

References 23 publications

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“…6 Regarding boron-site substitutions, Plešek et al disclosed in their pioneering work a dioxane ring-cleavage reaction that opened up a generic route to a series of COSAN derivatives. 26 Direct halogenation [27][28][29][30] and other substitutions at the B8 and B8′ positions have also been studied. [31][32][33] Regarding substitutions at the acidic carbon vertices, Grüner et al published the direct alkylation of COSAN with either formaldehyde or constrained cyclic ethers to make hydroxy derivatives versatile reagents for further derivatization.…”

Section: Introductionmentioning

confidence: 99%

Synthetic routes to carbon substituted cobalt bis(dicarbollide) alkyl halides and aromatic amines along with closely related irregular pathways

Nekvinda,

Bavol,

Litecká

et al. 2024

Dalton Trans.

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Section: Introductionmentioning

confidence: 99%

Synthetic routes to carbon substituted cobalt bis(dicarbollide) alkyl halides and aromatic amines along with closely related irregular pathways

Nekvinda,

Bavol,

Litecká

et al. 2024

Dalton Trans.

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“…Such systems typically comprise mono or disubstituted carborane derivatives, with rare examples of trisubstitution. Carbon‐substituted carboranes are generally prepared using either substituted alkynes or through metal mediated cross coupling reactions . A review was published recently detailing much of the work in this area .…”

Section: Methodsmentioning

confidence: 99%

Catalyst‐Free Polyhydroboration of Dodecaborate Yields Highly Photoluminescent Ionic Polyarylated Clusters

Lee

2016

Angewandte Chemie

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The incorporation of polyhedral boranes into novel photoluminescent materials is an area with increasing interest. While the neutral carboranes have been widely investigated for this purpose, the dodecaborate ion has received much less attention. Herein we report a significant expansion to the scope of substitution reactions for the dodecaborate ion, whereby this cluster was observed to react directly with a wide range of arenes in a step-wise and controlled manner. In the products of these reactions, the dodecaborate ion serves as a core upon which up to nine mono-or polycyclic aromatic hydrocarbon ligands are exohedrally bonded. Spectroscopic evidence suggests the presence of conjugation between the p systems of the aryl ligands and the dodecaborate core, resulting in materials which exhibit high solution-phase photoluminescence, as well as molar absorptivities and Stokes shifts that are significantly larger than those of the free arenes from which they were derived. We propose that this broad reactivity is a valuable synthetic tool for the incorporation of polyhedral boron into novel organic structures.

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“…Carbon-substituted carboranes are generally prepared using either substituted alkynes or through metal mediated cross coupling reactions. [10][11][12][13][14] A review was published recently detailing much of the work in this area. [15] Recently,the photophysical properties of salts of dodecaborate and its ether and amine derivatives have been reported.…”

mentioning

confidence: 99%

Catalyst‐Free Polyhydroboration of Dodecaborate Yields Highly Photoluminescent Ionic Polyarylated Clusters

Lee

2016

Angew Chem Int Ed

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The incorporation of polyhedral boranes into novel photoluminescent materials is an area with increasing interest. While the neutral carboranes have been widely investigated for this purpose, the dodecaborate ion has received much less attention. Herein we report a significant expansion to the scope of substitution reactions for the dodecaborate ion, whereby this cluster was observed to react directly with a wide range of arenes in a step-wise and controlled manner. In the products of these reactions, the dodecaborate ion serves as a core upon which up to nine mono- or polycyclic aromatic hydrocarbon ligands are exohedrally bonded. Spectroscopic evidence suggests the presence of conjugation between the π systems of the aryl ligands and the dodecaborate core, resulting in materials which exhibit high solution-phase photoluminescence, as well as molar absorptivities and Stokes shifts that are significantly larger than those of the free arenes from which they were derived. We propose that this broad reactivity is a valuable synthetic tool for the incorporation of polyhedral boron into novel organic structures.

show abstract

Skipping the one C–X one C–C bond rule in Kumada cross coupling reaction. Diarylation from an only B–I in metallacarboranes

Cited by 5 publications

References 23 publications

Synthetic routes to carbon substituted cobalt bis(dicarbollide) alkyl halides and aromatic amines along with closely related irregular pathways

Synthetic routes to carbon substituted cobalt bis(dicarbollide) alkyl halides and aromatic amines along with closely related irregular pathways

Catalyst‐Free Polyhydroboration of Dodecaborate Yields Highly Photoluminescent Ionic Polyarylated Clusters

Catalyst‐Free Polyhydroboration of Dodecaborate Yields Highly Photoluminescent Ionic Polyarylated Clusters

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