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Chapter
Dötz Reaction
Also known as the Dötz benzannulation, the Dötz reaction is the Cr(CO)3-coordinated hydroquinone from vinylic alkoxy pentacarbonyl chromium carbene (Fischer carbene) complex and alkynes.
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Chapter
Ferrier Glycal Allylic Rearrangement
In the presence of Lewis acid catalysts O-substituted glycal derivatives can react with O-, S-, C- and, less frequently, N-, P- and halide nucleophiles to give 2,3-unsaturated glycosyl products.1,2 This allylic t...
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Chapter
Schmidt Rearrangement
The Schmidt reactions refer to the acid-catalyzed reactions of hydrazoic acid with electrophiles, such as carbonyl compounds, tertiary alcohols and alkenes. These substrates undergo rearrangement and extrusion...
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Chapter
McMurry Coupling
Olefination of carbonyls with low-valent titanium such as Ti(0) derived from TiCl3/LiAlH4. A single-electron process.
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Chapter
Meerwein–Ponndorf–Verley Reduction
Reduction of ketones to the corresponding alcohols using Al(Oi-Pr)3 in isopropanol. Reverse of the Oppernauer oxidation
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Chapter
Birch Reduction
The Birch reduction is the 1,4-reduction of aromatics to their corresponding cyclohexadienes by alkali metals (Li, K, Na) dissolved in liquid ammonia in the presence of an alcohol.
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Chapter
Mukaiyama Reagent
Pyridinium halide reagent for esterification or amide formation.
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Chapter
Favorskii Rearrangement
Transformation of enolizable α-haloketones to esters, carboxylic acids, or amides via alkoxide-, hydroxide-, or amine-catalyzed rearrangements, respectively.
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Chapter
Sharpless Asymmetric Amino-hydroxylation
Osmium-mediated cis-addition of nitrogen and oxygen to olefins. Regio-selectivity may be controlled by ligand. Nitrogen sources (X-NClNa) include:
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Chapter
Smiles Rearrangement
Intramolecular nucleophilic aromatic rearrangement. General scheme:
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Chapter
Markovnikov’s Rule
For addition of HX to olefins, Markovnikov′s rule predicts the regiochemistry of HX addition to unsymmetrically substituted alkenes: The halide component of HX bonds preferentially at the more highly substitut...
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Chapter
Brook Rearrangement
Rearrangement of α-silyl oxyanions to α-silyloxy carbanions via a reversible process involving a pentacoordinate silicon intermediate is known as the [1,2]-Brook rearrangement, or [1,2]-silyl migration.
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Chapter
Buchwald–Hartwig Amination
The Buchwald–Hartwig amination is an exceedingly general method for generating an aromatic amine from an aryl halide or an aryl sulfonates. The key feature of this methodology is the use of catalytic palladium...
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Chapter
Neber Rearrangement
α-Aminoketone from tosyl ketoxime and base. The net conversion of a ketone into an α-aminoketone via the oxime.
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Chapter
Fries Rearrangement
Lewis acid-catalyzed rearrangement of phenol esters and lactams to 2- or 4-ketophenols. Also known as the Fries−Finck rearrangement.
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Chapter
Sharpless Asymmetric Epoxidation
Enantioselective epoxidation of allylic alcohols using t-butyl hydroperoxide (TBHP), titanium tetra-iso-propoxide, and optically pure diethyl tartrate (DET).
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Chapter
Sonogashira Reaction
Pd/Cu-catalyzed cross-coupling of organohalides with terminal alkynes. Cf. Cadiot–Chodkiewicz coupling and Castro-Stephens reaction. The Castro–Stephens coupling uses stoichiometric copper, whereas the Sonogashir...
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Chapter
Bucherer–Bergs Reaction
Formation of hydantoins from carbonyl compounds with potassium cyanide (KCN) and ammonium carbonate [(NH4)2CO3] or from cyanohydrins and ammonium carbonate. It belongs to the category of multiple component reacti...
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Chapter
Cadiot–Chodkiewicz Coupling
Bis-acetylene synthesis from alkynyl halides and alkynyl copper reagents.
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Chapter
Negishi Cross-Coupling Reaction
The Negishi cross-coupling reaction is the nickel- or palladium-catalyzed coupling of organozinc compounds with various halides or triflates (aryl, alkenyl, alkynyl, and acyl).
