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. Author manuscript; available in PMC: 2012 Nov 30.
Published in final edited form as: J Am Chem Soc. 2011 Nov 8;133(47):19020–19023. doi: 10.1021/ja209235d

Table 2. Nickel-Catalyzed Benzylation of Ethylenea.

graphic file with name nihms-337559-t0005.jpg
para-substituted
graphic file with name nihms-337559-t0006.jpg graphic file with name nihms-337559-t0007.jpg graphic file with name nihms-337559-t0008.jpg
graphic file with name nihms-337559-t0009.jpg graphic file with name nihms-337559-t0010.jpg graphic file with name nihms-337559-t0011.jpg
meta-substituted
graphic file with name nihms-337559-t0012.jpg graphic file with name nihms-337559-t0013.jpg graphic file with name nihms-337559-t0014.jpg
graphic file with name nihms-337559-t0015.jpg graphic file with name nihms-337559-t0016.jpg graphic file with name nihms-337559-t0017.jpg
hetero-substituted
graphic file with name nihms-337559-t0018.jpg graphic file with name nihms-337559-t0019.jpg graphic file with name nihms-337559-t0020.jpg
graphic file with name nihms-337559-t0021.jpg graphic file with name nihms-337559-t0022.jpg graphic file with name nihms-337559-t0023.jpg
ortho-substituted
graphic file with name nihms-337559-t0024.jpg graphic file with name nihms-337559-t0025.jpg graphic file with name nihms-337559-t0026.jpg
a

Isolated yield unless otherwise noted.

b

Determined by GC (internal standard).

c

Determined by 1H NMR spectroscopy (internal standard).

d

Yield obtained with 10 mol % catalyst.

e

2,3-Dihydro-1H-indene (4%) observed as inseparable byproduct.

f

Yield obtained with 20 mol % catalyst loading.

g

4-Cyano-β-methylstyrene (5%) obtained as an inseparable byproduct.

h

Obtained with 2.5 equiv Et3SiOTf.