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. 2022 Jul 20;7(30):26919–26927. doi: 10.1021/acsomega.2c03477

Table 1. Solvent, Temperature, and Substituents Effects on the Uncatalyzed Reaction between 1 and 2a.

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        conversion (%)
entry substrate T (°C) solvent 1 h 2 h 4 h
1 1a rt toluene 4 6 10
2 1a rt DCM 2 4 7
3 1a rt THF 5 6 9
4 1a rt iPrOH 7 11 20
5 1a rt tBuOAc 5 8 11
6 1a rt anisole 3 4 7
7 1a rt DMC 2 3 6
8 1c rt toluene 4 6 8
9 1f rt toluene 5 9 14
10 1h rt toluene 2 6 10
11 1i rt DCM 1 2 4
12 1j rt DCM 2 3 4
13 1l rt toluene 27 48 76
14 1l 0 toluene 3 6 12
15 1l –10 toluene 2 3 5
16 1n rt toluene 11 21 32
17 1o rt toluene 2 3 5
a

All reactions were carried out with 20 mol % excess of aldehyde, 0.5 M concentration, and the conversion was monitored by HPLC. The reported data are a selection of a more extended screening (see Supporting Information).