Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods

Mander, Lewis N.

doi:10.1016/b978-0-08-052349-1.00237-7

Cited by 22 publications

(7 citation statements)

References 130 publications

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“…The Meerwein arylation showcased the possibility of utilizing high-energy aryl radicals in the hydroarylation of olefins . The Birch reduction opened up a new dimension to the synthetic utility of arenes. , …”

Section: Introduction and Historical Contextmentioning

confidence: 99%

Radicals: Reactive Intermediates with Translational Potential

et al. 2016

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This Perspective illustrates the defining characteristics of free radical chemistry, beginning with its rich and storied history. Studies from our laboratory are discussed along with recent developments emanating from others in this burgeoning area. The practicality and chemoselectivity of radical reactions enable rapid access to molecules of relevance to drug discovery, agrochemistry, material science, and other disciplines. Thus, these reactive intermediates possess inherent translational potential, as they can be widely used to expedite scientific endeavors for the betterment of humankind.

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Section: Introduction and Historical Contextmentioning

confidence: 99%

Radicals: Reactive Intermediates with Translational Potential

et al. 2016

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“…The reduction of unsaturated hydrocarbons with alkali metal provides an interesting series of irreplaceable transformations in organic synthesis. The Birch reduction of aromatic rings is a representative, and it yields 1,4-cyclohexadienes by means of sodium metal in liquid ammonia . We envisioned that the Birch-type reduction is applicable to the borylation of PAHs, as illustrated in Scheme .…”

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confidence: 99%

Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons

2021

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Sodium dispersion promotes the reductive borylation of polycyclic aromatic hydrocarbons (PAHs) with MeOBpin. Anthracenes and phenanthrenes are converted to the corresponding dearomatized diborylated products. The reductive diborylation of naphthalene-based small π-systems yields similar yet unstable products that are oxidized into formal C–H borylation products with unique regioselectivity. Pyrene is converted to 1-borylpyrene without the addition of an oxidant. The latter two reactions represent a new route to useful borylated PAHs that rivals C–X borylation and catalytic C–H borylation.

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“…[80] The details of this synthesis, which showcases the utility of benzenoid synthons, [81] started with a Birch reduction [82] alkylation protocol. [83] The dianion of 2,5-dimethoxybenzoic acid (117) was generated via lithiumammonia reduction, and then quenched with 3-methoxybenzyl bromide (118) to give the dearomatised bis-enol ether 119. Double protonolysis and cyclisation of 119 with sulfuric acid gave a benzobicyclo[3.3.1]nonane (120), which underwent decarboxylation followed by methoxymethyl (MOM) protection of the bridgehead hydroxyl (i.e.…”

Section: Chemical Degradationmentioning

confidence: 99%

The Future of Retrosynthesis and Synthetic Planning: Algorithmic, Humanistic or the Interplay?

Williams

Dallaston

2021

Aust. J. Chem.

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The practice of deploying and teaching retrosynthesis is on the cusp of considerable change, which in turn forces practitioners and educators to contemplate whether this impending change will advance or erode the efficiency and elegance of organic synthesis in the future. A short treatise is presented herein that covers the concept of retrosynthesis, along with exemplified methods and theories, and an attempt to comprehend the impact of artificial intelligence in an era when freely and commercially available retrosynthetic and forward synthesis planning programs are increasingly prevalent. Will the computer ever compete with human retrosynthetic design and the art of organic synthesis?

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Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods

Cited by 22 publications

References 130 publications

Radicals: Reactive Intermediates with Translational Potential

Radicals: Reactive Intermediates with Translational Potential

Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons

The Future of Retrosynthesis and Synthetic Planning: Algorithmic, Humanistic or the Interplay?

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