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. 2019 Jan 9;17(8):2110–2115. doi: 10.1039/c8ob02899k

Table 1. Deprotection condition screening.

Inline graphic
Entry Conditions Time/h Conversion a /%
1 KI (2 equiv.) 24
2 KBr (2 equiv.) 24
3 KCl (2 equiv.) 24
4 KF (2 equiv.) 24 <1
5 KI (2 equiv.), 18-C-6 (3 equiv.) 24 <1
6 KF (2 equiv.), 18-C-6 (3 equiv.) 24 1
7 NaI (2 equiv.), 18-C-6 (3 equiv.) 24 <1
8 KF (2 equiv.), 18-C-6 (3 equiv.), methyl thioglycolate (10 equiv.) 1 78
9 KF (2 equiv.), methyl thioglycolate (10 equiv.) 1 61
10 KF (1 equiv.), 18-C-6 (1 equiv.), methyl thioglycolate (2 equiv.) 1 57
11 Methyl thioglycolate (10 equiv.) 24 <1
12 Methyl thioglycolate (10 equiv.). K2CO3 (2 equiv.) 24 90

aConversion was determined by 1H NMR analysis of the reaction mixture (see ESI). All reactions were carried out in a water bath set to 50 °C.