September Chemistry News

TCI Chemistry News September 2020




TCI offers an extensive catalog of 30,000 high quality organic chemicals suitable for benchtop-to-bulk chemistry. This issue covers our chemistry expertise in diamidite for the synthesis of phosphodiesters, a versatile reagent for sulfoximidation, quaternary ammonium salts, the Pauson-Khand reaction, and more.

Diamidite for the Synthesis of Phosphodiesters

Diamidite for the Synthesis of Phosphodiesters

Benzyl N,N,N',N'-tetraisopropylphosphorodiamidite [B5997] is used in the synthesis of phosphodiesters and phosphorylation of inositols and nucleosides. B5997 promptly reacts with alcohols in the presence of a base like 1H-tetrazole to afford a phosphoramidite. It can further react with another alcohol resulting in a phosphite triester with different alcohol species. Successive oxidation of the phosphorus atom and deprotection gives a phosphodiester.

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Versatile Reagent for Sulfoximidation

Versatile Reagent for Sulfoximidation

Dimethylsulfoximine [D4971] is a building block for the synthesis of sulfoximines and utilized in various types of sulfoximidation reactions. Possible applications include as SN2 reactions, nucleophilic attacks to carbonyl groups and cross-coupling reactions, providing  the target compounds in high yields under various conditions. Furthermore, this functional group can be inserted at a late stage of complex syntheses via C-H activation.
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Quaternary Ammonium Salts

Quaternary ammonium salts are organic compounds in which the ammonia molecule is tetrasubstituted with carbon and has a cationic state. A lot of quaternary ammonium salts have been synthesized and various applications have been reported in the literature. For example, in organic chemistry, tetramethylammonium hydroxide (TMAH) [T0676] as a methyl esterification agent, tetraethylammonium hydroxide (TEAH) [I0363] as an ion-pair reagent, tetrabutylammonium hydroxide (TBAOH) [T0717] as a polymerization catalyst, and benzyltriethylammonium chloride (BTEAC) [B0444] as a phase transfer catalyst have been reported.

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Pauson-Khand Reaction

Pauson-Khand Reaction

The Pauson-Khand reaction is a [2+2+1] type cyclization reaction used to construct a cyclopentenone moiety from alkynes and alkenes, mediated by dicobalt octacarbonyl [D3213]. Alkynes have high affinity towards D3213 and form an alkyne-dicobalt intermediate which can be isolated. This intermediate then coordinates with an alkene followed by CO insertion to afford the cyclic product. In many cases, the Pauson-Khand reaction is used in the total synthesis of natural products bearing a cyclopentanone moiety.
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