Table 1.

Evaluation of Fluorinated Directing Group

entry	ester	conversionc	yieldd
1	2d, Rf = CF3	100%	45%
2	2e, Rf = C2F5	100%	68%
3	2f, Rf = C3F7	96%	78%
4	2g, Rf = CF2Ph	98%	75%
5	2h, Rf = C7F15	95%	84%(75%)e

^aConditions for hydrosilylation of ester: [Ir(cod)OMe]₂ (1.0 mol %), Et₂SiH₂ (4.0 equiv), heptane (0.5 M), 60 °C, 24–48 h, N₂.

^bConditions for β-C(sp³)–H silylation: [Ir(cod)OMe]₂ (2.0 mol %), Me₄Phen (6.0 mol %), nbe (1.5 equiv), THF (0.1 M), 100 °C, 16 h, N₂.

^cConversion for the hydrosilylation step determined by ¹H NMR spectroscopy.

^dOverall yield for the two step determined by ¹H NMR spectroscopy using CH₂Br₂ as internal standard.

^eIsolated yield.