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. Author manuscript; available in PMC: 2014 Apr 10.
Published in final edited form as: J Am Chem Soc. 2013 Apr 2;135(14):5408–5419. doi: 10.1021/ja312148q

Scheme 2.

Scheme 2

Conditions: (a) CuI, 70 °C, 16 h, 1,10-phenanthroline, KCF3B(OMe)3, DMSO, 70%; (b) Pd2dba3, CuI, AsPh3, vinyltributyltin, dioxane, 50 °C, 2 h, 72%; (c) K4Fe(CN)6, Pd(OAc)2, KF, TBAB, H2O, microwave−150 °C, 15 min, 55%; (d) NaN3, CuI, N,N’-dimethylethylenediamine, 90 °C, 45 min, 74%; (e) MeONa 30% in MeOH, MeOH/CH2Cl2 8/2, 5 °C → rt, 45 min − 1 h: 10, 85%; 11, 90%; 12, 79%; 13, 98%; (f) proton sponge, POCl3, PO(OMe)3, −15 °C →−10 °C, 3 h then Bu3N, (Bu3NH)2H2P2O7 in DMF, −10 °C → 0 °C, 30 min then TEAB buffer (0.5M), rt, 10 min: 14, 20%; 15, 36%; 16, 42%; 17, 25%.