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. 2014 Jul 30;20(36):11540–11548. doi: 10.1002/chem.201403293

Table 2.

Thiol nucleophile scope

Inline graphic
Entry T [°C] Thiol2 Product Yield [%][a]
1 35 Inline graphic 3 a 70
2 35 Inline graphic 3 b 62
3 35 Inline graphic 3 c 76
4 35 Inline graphic 3 d 71
5 35 Inline graphic 3 e 66
6 35 Inline graphic 3 f 64
7 35 Inline graphic 3 g 68
8 35 Inline graphic 3 h 73
9 35 Inline graphic 3 i 49
10 35 Inline graphic 7 j 42
11[b] 50 BnSH 2 j 3 j 56
12[b] 50 nBuSH 2 k 3 k 47
13 60 Inline graphic 3 l 40
14[b] 60 CySH 2 l 3 l 56
15[b] 50 Inline graphic 3 n 45
16[b] 45 Inline graphic 3 o 92[c]

[a] Isolated yield. Regioselectivity SN2′/SN2>20:1 unless otherwise stated. [b] Resin-bound scavenger Reaxa QuadraPure™ MPA added at the end of reaction. [c] Formal SN2′/SN2 ratio 18:1.