Posts by Category: Reactions

Hauser-Kraus Annulation

Hauser-Kraus Annulation

General Characteristics The synthesis of naphthalene hydroquinones from phthalide anions and α,β–undaturated carbonyl compounds through the Michael addition-then-Dieckmann condensation is known as ...

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Davis Oxidation

Davis Oxidation

General Characteristics Ketones and esters can be hydroxylated at the α-position when their enolates are treated with 2-sulfonyloxaziridine (N-sulfonyloxaziridine, the Davis reagent). Asymmetric ...

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MSH Reagent

MSH Reagent

General Characteristics MSH (O-(mesitylsulfonyl)hydroxylamine) is an electrophilic aminating agent used to introduce a NH2 unit. It is used in reactions such as the Beckmann rearrangement, the Neber ...

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Hartwig-Miyaura C-H Borylation

Hartwig-Miyaura C-H Borylation

General Characteristics Iridium catalysts coordinated with electron-donating bidentate ligands promote direct C-H borylation of non-halogenated aromatic rings. Organoboronate compounds are, of ...

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Marshall Propargylation

Marshall Propargylation

General Characteristics  In the Marshall propargylation, propargyl mesylates and aldehydes are reductively coupled to form a new carbon-carbon bond. The transfer of chirality from the mesylates ...

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Rubottom Oxidation

Rubottom Oxidation

General Characteristics The epoxidation of silyl enol ethers with oxidants such as mCPBA and dioxirane leads to rearrangement into α-silyloxyketones. This reaction is used commonly to introduce a ...

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Oxidation with Dioxiranes

Oxidation with Dioxiranes

General Characteristics Dimethyldioxirane (DMDO), prepared from acetone and Oxone®, is used frequently to oxidize alkenes to epoxides. Methyl(trifluoromethyl)dioxirane (TFDO) is about 600 times more ...

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Shi Asymmetric Epoxidation

Shi Asymmetric Epoxidation

General Characteristics The asymmetric epoxidation of alkenes using the in situ generated chiral dioxirane formed from the fructose-derived ketone pre-catalyst and Oxone® (potassium ...

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Oxidative Coupling of Enolates

Oxidative Coupling of Enolates

General Characteristics Enolate species undergo dimerization under appropriately chosen oxidative conditions. Homo-coupling usually predominates, but there are successful examples of controlled ...

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Kharasch-Sosnovsky Oxidation

Kharasch-Sosnovsky Oxidation

General Characteristics Allylic C-H oxidation can be effected using acylperoxide under copper-catalyzed conditions. The alkene starting materials are usually used in excess. The terminal olefins are ...

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