Posts by Category: Reactions

SnAP Reagent

SnAP Reagent

General Characteristics SnAP (Sn(tin) Amine Protocol) reagents provide an easy access to a variety of saturated heterocycles and amines containing a spiro skeleton. The simple two-step procedure ...

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Krapcho Decarboxylation

Krapcho Decarboxylation

General Characteristics β-Keto methyl esters undergo decarboxylation under near neutral conditions upon heating in the presence of lithium chloride in DMSO. This reaction is particularly useful when ...

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Marko-Lam Deoxygenation

Marko-Lam Deoxygenation

General Characteristics The deoxygenation of alcohols via p-toluic acid esters under single-electron reduction conditions is known as the Marko-Lam deoxygenation. It has advantages over the ...

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Pomeranz-Fritsch Isoquinoline Synthesis

Pomeranz-Fritsch Isoquinoline Synthesis

General Characteristics The condensation of benzaldehydes or arylketones with aminoacetaldehyde acetals gives isoquinolines. Alternatively, the condensation of benzylamines with glyoxal hemiacetals ...

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Liebeskind-Srogl Cross Coupling

Liebeskind-Srogl Cross Coupling

General Characteristics Ketones can be synthesized by the palladium-catalyzed cross coupling between thioesters and boronic acids. The use of copper thiophene-2-carboxylate (CuTC) as an additive is ...

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Polonovski Fragmentation

Polonovski Fragmentation

General Characteristics The acylation of amine N-oxides with acid chlorides or acid anhydrides leads to bond fragmentation at the α-position, yielding the corresponding amides and aldehydes as ...

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Regitz Diazo Transfer

Regitz Diazo Transfer

General Characteristics Activated methylene compounds react with sulfonyl azides and related reagents to give the corresponding diazo compounds. These diazo compounds are used as 1,3-dipoles or ...

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Paal-Knorr Thiophene Synthesis

Paal-Knorr Thiophene Synthesis

General Characteristics The condensation of 1,4-dicarbonyl compounds with sulfur sources gives thiophenes. Phosphorus pentasulfide (P4S10) and the Lawesson’s reagent are typically used as the sulfur ...

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Boyland-Sims Oxidation

Boyland-Sims Oxidation

General Characteristics Anilines can be converted into aminophenols by the reaction called the Boyland-Sims oxidation. Ortho-hydroxylated products are usually obtained preferentially. The oxidation ...

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Mukaiyama Condensation Reagent

Mukaiyama Condensation Reagent

General Characteristics First introduced in 1970’s, 2-halo-N-alkylpyridinium salts are called the Mukaiyama reagent and used for condensation reactions such as esterification and amide bond ...

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