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. 2022 Nov 4;87(22):15693–15702. doi: 10.1021/acs.joc.2c02205

Table 1. Optimization of the Reaction Conditions for the Reductive Cyclization.

graphic file with name jo2c02205_0007.jpg

entry solvent T (°C) time base yield (%)
1 THF 70 5 h CH(NMe)3 (5 equiv) 0
2 THF 70 5 h CH(NMe)2Ot-Bu (3 equiv) 0
3 DMF rt 18 h TBAF (2 equiv) + HMPA (6 equiv) 13
4 DMF 150 4 h K2CO3 (2 equiv) + CuI (1 equiv) 37
5 DMF 150 4 h K2CO3 (2 equiv) 36
6 DMF 150a 15 min K2CO3 (2 equiv) 40
7 DMF 150a 15 min K2CO3 (4 equiv) 44
8 NMP 150a 15 min K2CO3 (4 equiv) 50
9 NMP 100a 15 min K2CO3 (4 equiv) 29
10 NMP 200a 15 min K2CO3 (4 equiv) 34
11 NMP 150a 15 min K2CO3 (10 equiv) 55
12 NMP 150 1 h K2CO3 (10 equiv) 50
13 NMPb 150 1 h K2CO3 (10 equiv) 82
14c NMPb 150 1 h K2CO3 (10 equiv) 87
a

Use of microwaves.

b

Concentration = 0.01 M.

c

The reaction was carried out on a 1 mmol scale.