Science of Synthesis

Huang, H.; Deng, G.-J.; Ji, X., Science of Synthesis Knowledge Updates, (2024) 2, 451.

General methods for the synthesis of mono-, di-, or trisilylated amidines still rely on the reactions of chlorotrimethylsilane with N-monosubstituted or N,N- or N,N′-disubstituted amidine lithium salts (see Section 22.4.9.1.1.1).[‌2‌] Very few new methods have been developed. Terephthalamide dioxime derivative ‌1‌ can be directly silylated with tert-butyldimethylsilyl chloride in dimethylformamide/triethylamine at room temperature to afford the tetrasilylated terephthalamide dioxime ‌2‌ in 30% yield (‌Scheme 1‌).[‌3‌] This method obviates the need for N-substituted amidine lithium salts.

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