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. Author manuscript; available in PMC: 2022 Oct 15.
Published in final edited form as: Org Lett. 2021 Oct 6;23(20):7927–7932. doi: 10.1021/acs.orglett.1c02307

Table 1.

Investigation of Pd Precursors for OAC Formationa

graphic file with name nihms-1814586-t0002.jpg
Entry Pd Precursor L Temp (°C) Yield A (%) Yield B (%)
1b P1 RuPhos rt n/a 99
2b P1 XPhos rt n/a 97
3b P1 t-BuXPhos rt n/a 99
4b P2 RuPhos rt n/a 98
5b P2 XPhos rt n/a 99
6b P2 t-BuXPhos rt n/a 40
7 P3 RuPhos rt 99 0
8 P3 XPhos rt 70 0
9 P3 t-BuXPhos rt 0 10
10 P3 t-BuBrettPhos rt 0 0
11 P3 RuPhos 60 41 59
12 P3 XPhos 60 0 99
13 P3 t-BuXPhos 60 0 82
14 P3 t-BuBrettPhos 60 0 24
graphic file with name nihms-1814586-t0003.jpg
a

Yields determined by 1H NMR using 0.5 equiv of 1,3,5-trimethoxybenzene as an internal standard. Reaction conditions: Pd precursor (0.05 mmol), L (0.055 mmol), aryl bromide (0.075 mmol), and THF (0.50 mL, 0.10 M).

b

Reactions run for 16 h.