Han, YifengMa, YunKeresztes, IvanCollum, David B.Corey, E. J.2015-09-012014Han, 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.1523-7060http://nrs.harvard.edu/urn-3:HUL.InstRepos:21461238Benzylic 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.en-USJournal Article2015-09-0110.1021/ol502348y