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. Author manuscript; available in PMC: 2015 Sep 8.
Published in final edited form as: Chemistry. 2014 Jul 30;20(37):11726–11739. doi: 10.1002/chem.201402353

Table 6.

Chemoselective Suzuki-Miyaura cross-coupling of 2-B(pin)-substituted allylic acetates with aryl bromides.

graphic file with name nihms626785u6.jpg
Entry Acetate Ar-Br Product Yield (%)[a]
1 1a Ph-Br graphic file with name nihms626785t57.jpg 6a 73
2 1a 4-MeO-C6H4-Br graphic file with name nihms626785t58.jpg 6b 54
3 1a 4-O2N-C6H4-Br graphic file with name nihms626785t59.jpg 6c 91
4 1a 4-F3C-C6H4-Br graphic file with name nihms626785t60.jpg 6j 85
5 1a 2-MeO-C6H4-Br graphic file with name nihms626785t61.jpg 6k 80
6 1b Ph-Br graphic file with name nihms626785t62.jpg 6d 87
7 1d 4-O2N-C6H4-Br graphic file with name nihms626785t63.jpg 6f 90
8 1f 4-O2N-C6H4-Br graphic file with name nihms626785t64.jpg 6h 80[b]
9 1a graphic file with name nihms626785t65.jpg graphic file with name nihms626785t66.jpg 6l 74
10 1a graphic file with name nihms626785t67.jpg graphic file with name nihms626785t68.jpg 6m 82
[a]

Yield of isolated and purified products.

[b]

The reaction was conducted at 75 °C in THF/H2O (10:1).