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. 2024 Nov 6;4(11):4223–4233. doi: 10.1021/jacsau.4c00899

Table 1. Optimization of Reaction Conditionsa.

graphic file with name au4c00899_0008.jpg

Entry Variation of standard condition Yieldb
1 None 85%(E/Z = 1:2)
2 K2CO3 instead of LiOH 29%
3 TMG instead of LiOH 72%
4 Pd(PPh3)2Cl2 instead of Pd(PPh3)4 79%
5 Pd2(dba)3 instead of Pd(PPh3)4 19%
6 MeCN instead of THF 43%
7 no XantPhos 28%
8 no (o–OMe)Ph2PPh 72%
9 no Pd(PPh3)4 N.D.
10 in the dark N.D.
11 no LiOH trace
12 0.3 mmol scale 91%c(E/Z = 1:2)
a

Reaction conditions: 1 (0.30 mmol), 2 (0.15 mmol), 3 (0.45 mmol), Pd(PPh3)4 (1.5 mol%), XantPhos (8 mol%), [(o-OMe)Ph]2PPh (8 mol%), LiOH (0.15 mmol), THF (0.1 M), λmax = 440 nm Kessil (40 W), N2, RT – 40 °C, 6 h.

b

GC yield with 1,3,5-trimethylbenzene as internal standard.

c

12 h, isolated yield. N.D., not detected.