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Wide selection of metal alkoxides allows conditions to be fine-tuned to the desired reaction

Alkali metal alkoxides reagents are moderate-to-strong bases that are used in drug and chemical synthesis applications, such as alkylation, arylation, acylation, solvolysis of esters, condensation, elimination, isomerization, rearrangements, transfer hydrogenation, Wittig reactions, and redox reactions. The reactivity can be fine-tuned to the desired reaction by the correct choice of alcoholate and counterion, solvent and temperature. The wide range of properties and solubilities of the bases allows for process optimization, improved selectivity and higher yields (table 1).

Table. 1. CALLERY™ Alkali metal alkoxides

The base strength can be varied with the structure of the alcohol and choice of solvent. As alkyl groups are added to the alcohol, the alkoxide anion becomes a stronger base compared to primary alkoxides and hydroxide. Furthermore, the higher base strength and steric bulk of the tertiary alkoxides influence the speed, selectivity, and specificity. Larger steric bulk of the alkoxide reduces the nucleophilicity of the anion, decreasing the number of undesired reactions.

Alkoxide bases are a key part of the organic chemist’s toolbox as well as reagents for synthesis of catalysts and inorganic materials. In addition, CALLERY™ alkoxide bases contain very low hydroxide content to help maximize yield and minimize by-products. A wide range of nucleophilic and non-nucleophilic bases are available for your applications.

For more information, please review the corresponding individual technical notes.