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. Author manuscript; available in PMC: 2008 Sep 15.
Published in final edited form as: J Am Chem Soc. 2006 Nov 29;128(47):15050–15051. doi: 10.1021/ja0647708

Table 1.

Catalytic carbometalation of propargylic alcohol 1a.a

graphic file with name nihms63700f3.jpg
entry CH3M catalystb ligandb conv. (%)c 2a/3ad
1 CH3MgBr CuBr none <5 ---
2 CH3MgBr Co(OAc)2 none 58 9/1
3 CH3MgBr Ni(acac)2 none 63 9/1
4 CH3MgBr Fe(acac)3 none 98 6/1
5e CH3MgBr Fe(ehx)3 none 98 5/1
6 CH3MgBr Fe(acac)3 dppe 97 21/1
7 CH3Li Fe(acac)3 none 0 ---
a

Reactions were carried out on 0.1 mmol scale under a N2 for 7 h.

b

20 mol%.

c

Determined by GC using an internal standard.

d

Determined by GC analysis of crude reaction mixture.

e

ehx = 2-ethyl hexanoate