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. Author manuscript; available in PMC: 2024 Mar 28.
Published in final edited form as: Can J Chem. 2023 Aug 30;101(10):765–772. doi: 10.1139/cjc-2023-0033

Table 3.

Exploration of additives in the synthesis of X1.

graphic file with name nihms-1932996-t0003.jpg
Entry Additive Drya Wetb Dioxane/water 4:1
1 Ca(NTf2)2 4 24 60
2 B(OMe)3 8 31 54
3 LiBF4 - - 65
4 DBU 7 — 71
5 NBu4Cl 0 — 22
6 NBu4Br 0 — 30

Note: Reaction conditions: PyFluor (0.3 mmol), 2-thiopheneboronic acid pinacol ester (0.45 mmol), Pd(dppf)Cl2 (0.03 mmol), Na3PO4 (0.9 mmol), additive (0.3 mmol), biphenyl (internal standard, 0.06 mmol), and solvent mixture (1 mL in a closed 1 dram vial).

a

Dioxane was degassed by three cycles of freeze–pump–thaw and dried under molecular sieves (10% v/w) for 48 h before using it.

b

Solvent was used as purchased. Yield calculated using biphenyl as internal standard (HPLC/UV).