Preferential Geminal Bis-silylation of 3,4-Benzothiophane Is Caused by the Dominance of Electron Withdrawal by R3Si over Steric Shielding Effects

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Han, Yifeng
Ma, Yun
Keresztes, Ivan
Collum, David B.
Corey, E. J.
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https://doi.org/10.1021/ol502348yMetadata
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Han, Yifeng, Yun Ma, Ivan Keresztes, David B. Collum, and E. J. Corey. 2014. “Preferential Geminal Bis-silylation of 3,4-Benzothiophane Is Caused by the Dominance of Electron Withdrawal by R3Si over Steric Shielding Effects.” Organic Letters 16 (17): 4678-4679. doi:10.1021/ol502348y. http://dx.doi.org/10.1021/ol502348y.Abstract
Benzylic C–H lithiation of 3,4-benzothiophane and subsequent treatment with triphenyl- or trimethylchlorosilane under a variety of conditions leads to α,α- rather than α,α′-bis-silylation products as a consequence of anion stabilization by R3Si and very fast deprotonation of the intermediate monosilylated product, even with a sterically bulky base such as lithium diisopropylamide.Other Sources
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4176386/pdf/Terms of Use
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