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. 2020 Jun 12;10(14):7449–7463. doi: 10.1021/acscatal.0c01343

Table 1. Optimization of the Reaction Conditions for the Formation of 1, Catalyzed by PPh4[CoIII(TAMLred)] or [CoIII(TAMLsq)]e.

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entry catalyst loading (mol %) solvent concentration PhINNs (mM) (time, h) yield (%)
PPh4[CoIII(TAMLred)]
1 5.0 toluene 48 (16) 40
2 5.0 benzene 48 (16) 41
3 5.0 MeCN 48 (16) 18
4 5.0 CH2Cl2 48 (16) 58
5a 5.0 CH2Cl2 48 (16) 44
6 5.0 CH2Cl2 24 (16) 77
7 5.0 CH2Cl2 24 (2) 76
8 2.5 CH2Cl2 24 (2) 64
9b 2.5 CH2Cl2 24 (2) 67
10c CH2Cl2 24 (2) 0
[CoIII(TAMLsq)]
11 5.0 toluene 48 (16) 7
12 5.0 CH2Cl2 48 (16) 57
13 5.0 CH2Cl2 24 (2) 74
14 2.5 CH2Cl2 24 (2) 35
15b 2.5 CH2Cl2 24 (2) d
a

1.0 equiv styrene was used.

b

Aerobic conditions.

c

No catalyst added.

d

[CoIII(TAMLsq)] is not stable under aerobic conditions.

e

Yields based on 1H NMR integration using 1,3,5-trimethoxybenzene as an internal standard..