Skip to main content
. Author manuscript; available in PMC: 2006 Aug 23.
Published in final edited form as: Org Lett. 2005 Oct 13;7(21):4585–4588. doi: 10.1021/ol051700h

Table 1.

Synthesis of Syn N-Donor Ligands 5a–i

graphic file with name nihms5640t1.jpg

entry ArXb-d product yield (%) (overall yield)e
1 graphic file with name nihms5640t2.jpg 5a 93 (47)f
2 graphic file with name nihms5640t3.jpg 5b 79 (40)f
3 graphic file with name nihms5640t4.jpg 5c 97 (40)f
4 graphic file with name nihms5640t5.jpg 5d 93 (49)f
5 graphic file with name nihms5640t6.jpg 5e 80 (47)d
6 graphic file with name nihms5640t7.jpg 5f 99 (50)f,g
7 graphic file with name nihms5640t8.jpg 5g 87 (44)f,g
8 graphic file with name nihms5640t9.jpg 5h 67 (9)h
9 graphic file with name nihms5640t10.jpg 5i 63 (32)f
a

2.2–2.5 equiv of ArX was used.

b

10 mol % of Pd(PPh3)4, Et3N, THF, 55 °C.

c

10 mol % of PdCl2(PPh3)2, 5 mol % of CuI, Et3N, THF, rt.

d

10 mol % of PdCl2(PPh3)2, piperidine, 65 °C.

e

The overall yield is calculated for the longest linear sequence from commercially available materials.

f

Overall yield from 1,2,4,5-tetrabromobenzene.

g

The yield was measured by 1H NMR spectroscopy using an internal standard.

h

Overall yield from anthranilic acid.