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. Author manuscript; available in PMC: 2019 Jan 19.
Published in final edited form as: Org Lett. 2018 Jan 5;20(2):357–360. doi: 10.1021/acs.orglett.7b03591

Table 1.

Optimizationa

graphic file with name nihms941115u2.jpg
no 1 cat. ligand base deviation from standard conditions Yield of 3ab (%)
1 1a Pd(PPh3)4 - Cs2CO3 toluene, 50 °C dec.
2 1a Pd(dppf)Cl2 - Cy2NMe PhCF3, 110 °C dec.
3 1a Pd(OAc)2 Xantphos Cs2CO3 - 87
4 1a Pd(PPh3)4 - Cs2CO3 THF 14
5 1a Pd(OAc)2 DPEPhos Cs2CO3 - 7
6 1a Pd(OAc)2 t-Bu-Xantphos Cs2CO3 - 0
7 1a Pd(OAc)2 L Cs2CO3 - 7
8 1a Pd(OAc)2 Xantphos Cs2CO3 no light, 40 °C traces
9 1a - Xantphos Cs2CO3 - 0
10 1d Pd(dppf)Cl2 - Cy2NMe PhCF3, 110 °C dec.
11 1d Pd(OAc)2 Xantphos Cs2CO3 - 67
12 1d Pd(OAc)2 Xantphos Cs2CO3 no light, rt 88
13 1h Pd(dppf)Cl2 - Cy2NMe PhCF3, 110 °C dec.
14 1h Pd(OAc)2 Xantphos Cs2CO3 - 30
15 1h Xantphos Pd G3 - iPr2NEt - 86
16 1h Xantphos Pd G3 - iPr2NEt no light, 40 °C 96
a

Conditions: 1a 0.1 mmol scale, catalyst (10 mol %), ligand (20 mol %), base (2 equiv), benzene (0.5 M), 34 W blue LED.

b

GC–MS yield.