Table 3. Selectivity Based on Electronic Bias.
General reaction conditions: 1.0 equiv of aryl chloride, 0.13 M dioxane/H2O (2:1), 2.3 equiv of R2(CH2)2Bpin, 1 mol % Pd2(dba)3, 6 mol % FcPPh2, 6.0 equiv of K3PO4, 18–20 h, 100 °C.
Isolated yield.
1.5 equiv of R2(CH2)2Bpin, 3.0 equiv of K3PO4.
Not detected by 1H NMR.
Exhaustively coupled product (6% yield) was detected by crude 1H NMR.
48 h.
Isolated after reaction with trifluoroacetic acid.
2 mol % Pd2(dba)3, 12 mol % FcPPh2.