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. Author manuscript; available in PMC: 2021 Oct 28.
Published in final edited form as: Chem Rev. 2020 Sep 24;120(20):11479–11615. doi: 10.1021/acs.chemrev.0c00523

Figure 191.

Figure 191.

Regioselective derivatization of tribromides 10.26a using cross-coupling methodologies. Conditions: (a) 1 atm H2, 10 mass% Pd/C, MeOH (0.02 M), 12 h, 0 °C. (b) 2.0 equiv Ar–B(OH)2,10 mol% Pd2(dba)3, 20 mol% P(t-Bu)(Cy)2•HBF4, 4.0 equiv K3PO4, THF/H2O (3:1, 0.1 M), 45 °C, 24 h. (c) 2.0 equiv NHR2, 10 mol% Pd2(dba)3, 20 mol% rac-BINAP, 1.4 equiv NaOt-Bu, PhMe (0.1 M), 80 °C, 18 h.440