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. Author manuscript; available in PMC: 2010 Aug 12.
Published in final edited form as: J Am Chem Soc. 2009 Aug 12;131(31):11049. doi: 10.1021/ja903049z

Table 9.

Synthesis of Amides and Imides from Aryl Bromides and Chloridesa

graphic file with name nihms131741u9.jpg

entry aryl halide electrophile loading (%) T1 (°C)b T2 (°C)b product yield (%)c
1d graphic file with name nihms131741t85.jpg graphic file with name nihms131741t88.jpg 0.1 100 25 graphic file with name nihms131741t94.jpg 89
2 graphic file with name nihms131741t89.jpg 0.1 100 25 graphic file with name nihms131741t95.jpg 51
3d graphic file with name nihms131741t90.jpg 0.1 100 50 graphic file with name nihms131741t96.jpg 74
4 Boc2 0.1 100 80 graphic file with name nihms131741t97.jpg 75
5d graphic file with name nihms131741t86.jpg graphic file with name nihms131741t91.jpg 0.1 100 50 graphic file with name nihms131741t98.jpg 82
6d graphic file with name nihms131741t92.jpg 0.1 100 50 graphic file with name nihms131741t99.jpg 94
7 Boc2 0.1 100 80 graphic file with name nihms131741t100.jpg 68
8 graphic file with name nihms131741t87.jpg graphic file with name nihms131741t93.jpg 0.1 90 25 graphic file with name nihms131741t101.jpg 75
a

Reactions conducted with 1:1 ratio of metal to ligand.

b

Temperature of bath.

c

Isolated yield after purification by flash column chromatography.

d

1 equiv of Et3N was added.