Pyridyl group assisted deprotonation of a methyl group on silicon: Complex induced proximity effect and novel hydroxymethylation

K Itami, T Kamei, K Mitsudo, T Nokami…

文献索引：Itami; Kamei; Mitsudo; Nokami; Yoshida Journal of Organic Chemistry, 2001 , vol. 66, # 11 p. 3970 - 3976

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被引用次数: 52

摘要

A novel methodology for the deprotonation of a methyl group on silicon has been developed. This newly developed α-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the α-silyl carbanion together with the inherent silicon α effect. It was found that the deprotonation (t-BuLi/Et2O/-78° C) occurs with 2- pyridyltrimethylsilane but not with other related silanes such as phenyltrimethylsilane, 3- ...