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. Author manuscript; available in PMC: 2021 Jun 2.
Published in final edited form as: Angew Chem Int Ed Engl. 2020 Mar 24;59(23):9143–9148. doi: 10.1002/anie.202001824

Table 1.

Optimization of reaction conditionsa

graphic file with name nihms-1576748-t0005.jpg
entry deviation from standard GC yield (%)a,b
1 none 63
2 PC-2 instead of PC-1 11
3 PC-3 instead of PC-1 0
4 Az-2 instead of Az-1 14
5 Az-3 instead of Az-1 0
6 Az-4 instead of Az-1 0
7 Az-5 instead of Az-1 11
8 CsOAc instead of Cs2CO3 38
9 K2CO3 instead of Cs2CO3 8
10 Li2CO3 instead of Cs2CO3 0
11 CH3CN instead of THF 72
12 CH2CI2 instead of THF 41
13 DMF instead of THF 65
14 no light 0
15 no photocatalyst 0
16 no Az 0
17 no base 0
graphic file with name nihms-1576748-t0006.jpg
a

Gas chromatography (GC) yield is based on a calibration curve using 1,3,5-trimethoxybenzene as the internal standard.

b

Reaction conditions: 1a (0.10 mmol), Bn–HE 2a (0.15 mmol), Az (0.015 mmol), base (0.015 mmol), PC (1 μmol), solvent (0.1 M; THF, tetrahydrofuran; DMF, dimethyformamide) for 16 h.