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. 2024 Jan 21;15(9):3365–3371. doi: 10.1039/d3sc05796h

Optimization of the second step: solid-state ligand exchange of 3a with 2-phenylpyridine (2a) in the presence of silver salta.

graphic file with name d3sc05796h-u2.jpg
Entry Silver salt (2.0 equiv.) Time (min) Internal temp.b (°C) Yield (%) of 4ac
1 AgOTf 60 135 73
2 None 60 135 12
3 AgOTf 60 30 5
4 AgOTf 30 135 70
5 Ag2O 60 135 10
6 Ag2CO3 60 135 14
a

Conditions: 3a (0.05 mmol), silver salt (0.10 mmol), 2a (0.25 mmol), 2-methoxyethan-1-ol (0.20 μL mg−1) in a stainless-steel milling jar (1.5 mL) with a stainless-steel ball (5 mm).

b

The reaction temperature was controlled using a heat gun (for details, see the ESI). The internal temperature was confirmed by thermography immediately after opening the milling jar.

c

Isolated yields are shown.