Cross-coupling with Me3SiZnIa.
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a
2 eq. of 3; 1.2 eq. of Me3SiZnI·TMEDA 2b (0.56 M in toluene, 1.19 mmol); 10 mol% Ni(OAc)2·4H2O; 10 mol% dtbpy; 1,2-dimethoxy ethane (0.17 M).
b
NMR yield.
c
A decarbonylative byproduct was observed.
d
Dimerization of 3 to a diketone was observed.
e
Ni(COD)2 (10 mol%) instead of Ni(OAc)2·4H2O.
f
Decomposition on silica was observed.
g
Conditions: 2 eq. of 3, 1eq. of PhMe2SiZnI·TMEDA (0.71 M in toluene), 20 mol% of CuI, 1 eq. of LiCl, 1,2-dimethoxy ethane (0.15 M overall concentration), 0 °C – rt.
h
6 mmol of 2b was employed.
i
10 mol% Ni(OAc)2·4H2O, 10 mol% 1,10-phen, 20 mol% of CuI was added.