All RCYs are decay-corrected and averaged over three experiments unless otherwise noted. Asterisk indicates yield averaged over five experiments. Single-dagger symbol indicates that 24.8% RCY of the 2-fluoro dechlorinated product is formed. Double-dagger symbol indicates that the RCYs listed are based on the product deprotection yields (see SM 5.6). Bu, butyl; MeCN, acetonitrile; hex, hexyl; iPr, isopropyl; t-Bu, tert-butyl; Me, methyl; Ph, phenyl; OTf, trifluoromethanesulfonate; Et, ethyl; Boc, butoxycarbonyl.