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. Author manuscript; available in PMC: 2022 Sep 28.
Published in final edited form as: Tetrahedron Lett. 2021 Aug 21;81:153338. doi: 10.1016/j.tetlet.2021.153338

Table 1.

Hiyama cross-coupling of 4-TMS-triazoles.

graphic file with name nihms-1738950-t0002.jpg
Entry ArX 6 Catalyst mol % Temp (°C) Yield (%)a
1 4 6a Pd(PPh3)4 20 rt 3a, trace
2 5 6a Pd(PPh3)4 20 rt 3a, trace
3 5 6a Pd2(dba)3/P(o-tol)3 20 rt 3a, 0
4 5 6a PdCl2(dppe) 20 rt 3a, 12
5 5 6a PdCl2(dppp) 20 rt 3a, 15
6 5 6a PdCl2(dppb) 20 rt 3a, trace
7 5 6a PdCl2(dppf) 20 rt 3a, 0
8 5 6a PdCl2(BINAP) 20 rt 3a, 7
9 5 6a Pd2(dba)3/Xantphos 20 rt 3a, trace
10 5 6a PdCl2(dppp) 20 60 3a, 24
11b 5 6a PdCl2(dppp) 40 60 3a, 42
12b 5 6a PdCl2(dppp) 40 40 3a, 41
13b,c 5 6a PdCl2(dppp) 40 40 38,46d
14 b,c 5 6b PdCl2(dppp) 40 40 3b, 54d
15b,c 5 6c PdCl2(dppp) 40 40 3c, 31d
16b,c 5 6d PdCl2(dppp) 40 40 3d, 23d

0.1 mmol of 4 or 5 was used for entries 1 – 12. 6a(R = Bn), 6b (R = Mes), 6c (R = Bzh) & 6d (R = 1-ad).

a

1H NMR yield estimated with 1,1,2,2-tetrachloroethane as an internal standard unless otherwise noted.

b

4.8 equiv of 6, TBAF·3H2O, and Ag2O.

c

1 mmol scale reaction.

d

Isolated yield after flash chromatography on silica gel.