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. 2021 Nov 30;12(47):15719–15726. doi: 10.1039/d1sc06038d

Cross-coupling with PhMe2SiZnIa.

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a

Reaction conditions: 2 eq. of 3, 1.1 eq. of PhMe2SiZnI·TMEDA 2a (0.66 M in toluene), 5 mol% of Ni(OAc)2·4H2O, 5 mol% of dtbpy, 1,2-dimethoxy ethane (0.17 M).

b

Unreactive PhMe2SiZnI·TMEDA was observed as PhMe2SiH.

c

NMR yield.

d

Conditions: 2 eq. of 3, 1 eq. 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.

e

A decarbonylative byproduct was observed.

f

10 mol% Ni(OAc)2·4H2O, 10 mol% 1,10-phen, and 20 mol% of CuI were added.

g

The Brook rearrangement was observed.