Preferential Geminal Bis-silylation of 3,4-Benzothiophane Is Caused by the Dominance of Electron Withdrawal by R3Si over Steric Shielding Effects
Collum, David B.
Corey, E. J.
MetadataShow full item record
CitationHan, 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.
AbstractBenzylic 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.
Citable link to this pagehttp://nrs.harvard.edu/urn-3:HUL.InstRepos:21461238
- FAS Scholarly Articles