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. Author manuscript; available in PMC: 2009 Dec 15.
Published in final edited form as: Tetrahedron Lett. 2008 Dec 15;49(51):7307–7310. doi: 10.1016/j.tetlet.2008.10.039

Table 3.

Conditions for the selective oxidative boron-Heck reaction with 2-cyclohexen-1-one 9 a

graphic file with name nihms80640f5.jpg
entry mole ratio
Pd/ligand T (°C) time (h) yield (%)d
7 9
1b 1 1.2 5 mol % 23 16 61
2c 1 1.2 10 mol % 23 16 78
3c 1 2 10 mol % 23 16 80
4c 1 2 10 mol % 50 6 85
5c 1 1.2 10 mol % 50 6 65
a

All reactions were carried out with 7 (1.0 mmol) and various mole ratio of 2-cyclohexen-1-one in DMF (2.5 mL).

b

dmphen [2,9-dimethyl phenanthroline] (5.5 mol %).

c

dmphen [2,9-dimethyl phenanthroline] (11.0 mol %).

d

NMR yields.