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. Author manuscript; available in PMC: 2017 Aug 9.
Published in final edited form as: Chem Commun (Camb). 2017 Apr 27;53(35):4771–4774. doi: 10.1039/c7cc01606a

Table 1.

Optimization of Reaction Conditions

graphic file with name nihms883334u1.jpg
entry conditions Arene (equiv) Amine (equiv) T (°C) % conv
1. 0.3 M ACN a (2) DIPEA (3) 45 100
2. 0.3 M ACN a (2) DIPEA (3) 22 100
3. 0.3 M DMF a (2) DIPEA (3) 22 100
4. 0.3 M DMSO a (2) DIPEA (3) 22 100
5. 0.3 M THF a (2) DIPEA (3) 22 24
6. 0.3 M Tol a (2) DIPEA (3) 22 <5
7. 0.3 M DCM a (2) DIPEA (3) 22 25
8. 1 M ACN a (1.025) DIPEA (3) 22 100
9. 1 M ACN b (2) DIPEA (3) 22 <5
10. 1 M ACN b (2) TMG (2.4) −20 100
11. 1 M ACN b (1.025) TMG (2.05) −20 100
12. 1 M ACN a (1.025) TMG (2.05) −20 100
a

Conversion determined by 19F NMR after 30 min.