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. 2018 Apr 11;8(25):13643–13648. doi: 10.1039/c8ra01381k

Comparison of forward-order and reverse-order strategies in synthesis of unsymmetrical biaryl compoundsa.

graphic file with name c8ra01381k-u21.jpg
Entry Ar1–Cl Ar2–Cl Product Forward yieldb (%) Reverse yieldb (%)
1 graphic file with name c8ra01381k-u22.jpg graphic file with name c8ra01381k-u23.jpg graphic file with name c8ra01381k-u24.jpg 87 98
2 graphic file with name c8ra01381k-u25.jpg graphic file with name c8ra01381k-u26.jpg graphic file with name c8ra01381k-u27.jpg 84 25
3 graphic file with name c8ra01381k-u28.jpg graphic file with name c8ra01381k-u29.jpg graphic file with name c8ra01381k-u30.jpg 65 93
4 graphic file with name c8ra01381k-u31.jpg graphic file with name c8ra01381k-u32.jpg graphic file with name c8ra01381k-u33.jpg 91c 20
5 graphic file with name c8ra01381k-u34.jpg graphic file with name c8ra01381k-u35.jpg graphic file with name c8ra01381k-u36.jpg 77c 42c
6 graphic file with name c8ra01381k-u37.jpg graphic file with name c8ra01381k-u38.jpg graphic file with name c8ra01381k-u39.jpg 38d 79c
7 graphic file with name c8ra01381k-u40.jpg graphic file with name c8ra01381k-u41.jpg graphic file with name c8ra01381k-u42.jpg 35c 85c
a

General conditions: (a) first chloride (1.1 equiv.), XPhos-Pd-G2 (1.0 mol%), XPhos (1.0 mol%), B2pin2 (1.2 equiv.), K3PO4·7H2O (3.0 equiv.), EtOH (0.275 M), RT, 2 h; (b) second chloride (1.0 equiv.), 3.0 M aq. K3PO4·7H2O (3.0 equiv.), RT, 8 h.

b

Yield of isolated product.

c

15 h for the second step.

d

6 h for the second step.