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. Author manuscript; available in PMC: 2023 Sep 7.
Published in final edited form as: Nature. 2020 Jun 1;583(7817):548–553. doi: 10.1038/s41586-020-2399-1

Fig. 3 |. Scope of nucleophiles and electrophiles that participate in defluorinative alkylation reactions and transformations of the products.

Fig. 3 |

a, Nucleophilic lithium salts in defluorinative alkylation reactions. b, Silyl ketene acetals in defluorinative alkylation reactions. c, 3-Substituted 3,3-difluoropropenes in defluorinative alkylation reactions. d, Synthesis of fluorinated derivatives of medicinally active compounds from the substitution products. Isolated yields reported unless otherwise noted. a2 mol% Cω, −10 °C, 72 h. b96 h. c5 mol% Cω’, 0 °C, 72 h. d2 mol% Cω’, 5 equiv. LiBr, RT, 24 h. e6 mol% Cγ, 5 mol% NaCMe(CO2Et)2, RT, 48 h. ftert-Butyl dimethyl silyl ketene acetal, 6 mol% Cγ, RT, 53 h. g2 mol% TMSOTf, 4 mol% Cγ, dioxane, RT, 40 h. h5 mol% Cω’, 5 equiv. LiBr, RT, 48 h. i5 mol% Cω, 65 °C, 96 h. j2 mol% Cω, 3 equiv. Ba(OTf)2, RT, 19 h. k20 mol% Cω, 3 equiv. Ba(OTf)2, dioxane, RT, 24 h. EWG, electron-withdrawing group; TMS, trimethylsilyl; MOM, methoxymethyl; Bz, benzoyl; CSA, camphor sulfonic acid; DME, 1,2-dimethoxyethane; DMS, dimethylsulfide; 1-Np, 1-naphthyl; d.r., diastereometric ratio.