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. Author manuscript; available in PMC: 2014 Apr 5.
Published in final edited form as: Org Lett. 2013 Mar 14;15(7):1536–1539. doi: 10.1021/ol400320q

Table 1.

Suzuki-Miyaura Cross-Coupling of Various Aryl Halides with Dioxolanylethyltrifluoroborate 1 a

graphic file with name nihms-456440-f0005.jpg
entry electrophile product isolated yield (%)
1 graphic file with name nihms-456440-t0006.jpg graphic file with name nihms-456440-t0007.jpg 89 (Br)
82b (Br)
74 (Cl)
2 graphic file with name nihms-456440-t0008.jpg graphic file with name nihms-456440-t0009.jpg 56
3 graphic file with name nihms-456440-t0010.jpg graphic file with name nihms-456440-t0011.jpg 83
4 graphic file with name nihms-456440-t0012.jpg graphic file with name nihms-456440-t0013.jpg 48 (Br)
0c (Cl)
5 graphic file with name nihms-456440-t0014.jpg graphic file with name nihms-456440-t0015.jpg 70
6 graphic file with name nihms-456440-t0016.jpg graphic file with name nihms-456440-t0017.jpg 62
7 graphic file with name nihms-456440-t0018.jpg graphic file with name nihms-456440-t0019.jpg 90
8 graphic file with name nihms-456440-t0020.jpg graphic file with name nihms-456440-t0021.jpg 38 (Br)
82 (Cl)
9 graphic file with name nihms-456440-t0022.jpg graphic file with name nihms-456440-t0023.jpg 59
10 graphic file with name nihms-456440-t0024.jpg graphic file with name nihms-456440-t0025.jpg 71 (Br)
55 (Cl)
11 graphic file with name nihms-456440-t0026.jpg graphic file with name nihms-456440-t0027.jpg 50d
12 graphic file with name nihms-456440-t0028.jpg graphic file with name nihms-456440-t0029.jpg 68d
13 graphic file with name nihms-456440-t0030.jpg graphic file with name nihms-456440-t0031.jpg 69
14 graphic file with name nihms-456440-t0032.jpg graphic file with name nihms-456440-t0033.jpg 38e
a

Reaction conditions: Aryl halide (1.0 equiv), organotrifluoroborate (1.1 equiv), PdCl2AtaPhos2 (5 mol %), Cs2CO3 (3.0 equiv), toluene/H2O (4:1, [ ] = 0.25 M), 100 °C, 14 h.

b

Using 2.5 mol % catalyst.

c

A mixture of aryl chloride and boronic acid was recovered.

d

Product contains up to 8 % impurity.

e

Reaction performed on a 3 mmol scale using a 1 : 1 trifluoroborate/electrophile ratio and only 1 mol % Pd.