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Regio- and Stereoselective (SN2) N-, O-, C- and S-Alkylation Using Trialkyl Phosphates

Amit Banerjee*, Tomohiro Hattori*, Hisashi Yamamoto*

*Molecular Catalyst Research Center, Chubu University, Kasugai, Aichi 487-8501, Japan, Email:,,

A. Banerjee, T. Hattori, H. Yamamoto, Synthesis, 2023, 55, 315-332.

DOI: 10.1055/a-1504-8366

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Trialkyl phosphates are inexpensive and stable at room temperature, under air, and are easy to handle. Mild, straightforward and powerful methods for nucleophilic alkylation of various N-, O-, C- and S-nucleophiles using readily available trialkyl phosphates proceed smoothly in excellent yields. Stereoselective transfer of secondary alkyl groups have also been achieved with inversion of configuration.

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Key Words

trialkyl phosphates, stereoselectivity, SN2 reaction, amides (N-alkylation, C-alkylation), secondary alkylation, vinyl ethers

ID: J66-Y2023