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. 2020 Feb 5;31(3):770–780. doi: 10.1021/acs.bioconjchem.9b00863

Table 1. General Screening of Palladium Catalyst Systems.

graphic file with name bc9b00863_0006.jpg

entry catalyst base time solvent additive conversiona
1b A CsOH 100 °C, 3 h DMA N/A 75%
2c B NaOH 60 °C, 2 h DMA N/A 30%
3d C CsOH 95 °C, 25 min MIPO N/A 33%
4e C CsOH 95 °C, 25 min MIPO N/A 0%
5e C CsOH 95 °C, 25 min DMA N/A 6%
6f D CsOH 95 °C, 25 min MIPO N/A 0%
7f D CsOH 95 °C,25 min DMA N/A 14%
8g D CsOH 95 °C, 25 min DMA Na ascorbate 57%
9g D CsOH 95 °C, 15 min DMA Na ascorbate 63%
a

The conversion was determined by LC-MS.

b

Condition reported by GSK46.

c

Condition reported by Eli Lilly48.

d

Condition reported by BCM26.

e

Reaction conditions: 1 (5 nmol), 250 equiv of aniline (400 mM), 2 equiv of catalyst (5 mM), 500 equiv of CsOH (1000 mM), H2O (2.5 μL), solvent (4.9 μL).

f

Reaction conditions: 1 (5 nmol), 250 equiv of aniline (400 mM), 2 equiv of catalyst (5 mM), 500 equiv of CsOH (1000 mM), H2O (2.5 μL), solvent (4.9 μL).

g

Reaction conditions: 1 (5 nmol), 250 equiv of aniline (400 mM), 2 equiv of catalyst (5 mM), 500 equiv of CsOH (1000 mM), 20 equiv of sodium ascorbate (40 mM), DMA (4.9 μL). DMA = dimethylacetamide. MIPO = 1-methoxy-2-isopropanol.