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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 3.

Tandem allylic substitution/Suzuki-Miyaura cross-coupling of 2-B(pin)-substituted allylic acetates.

graphic file with name nihms626785u3.jpg
Entry Allylic acetate Nu/NuH Ar-X Product Yield (%)[a]
1 graphic file with name nihms626785t35.jpg
1a
graphic file with name nihms626785t36.jpg 4-Me-C6H4-Br graphic file with name nihms626785t37.jpg 5a 70
2 1a graphic file with name nihms626785t38.jpg 4-MeO-C6H4-Br 5b 65
3 1a graphic file with name nihms626785t39.jpg 3-C5H3N-Br 5c 52
4 graphic file with name nihms626785t40.jpg
1f
graphic file with name nihms626785t41.jpg Ph-I graphic file with name nihms626785t42.jpg 5d 50
5 1f graphic file with name nihms626785t43.jpg Ph-Br 5d 70
6 1f graphic file with name nihms626785t44.jpg 4-MeO-C6H4-Br 5e 69
7 1f graphic file with name nihms626785t45.jpg 4-O2N-C6H4-Br 5f 59
8 1f NaCH(CO2Me)2 Ph-I [b]
9 1f NaCH(CO2Me)2 Ph-Br graphic file with name nihms626785t46.jpg 5g 51
10 graphic file with name nihms626785t47.jpg
1h
NaCH(CO2Me)2 Ph-Br graphic file with name nihms626785t48.jpg 5h 61
[a]

Yield of purified and isolated products.

[b]

No cross-coupling product was observed, but 43% of 2h was isolated.