Table 2.
entry | substrate | product | timeb (h) | yieldc (%) |
1 | 1 | 85 | ||
2 | 1 | 94 | ||
3 | 1 | 80 | ||
4 | 1 | 95 | ||
5 | 1 | 98 | ||
6 | 1 | 95 | ||
7 | 1 | 99 | ||
8 | 1 | 99 | ||
9 | 3 | 98 (94) | ||
10 | 3 | 86 | ||
11 | 3 | 93 | ||
12 | 3 | 95 | ||
13 | 3 | 98 | ||
14 | 12 | 81d | ||
15 | 20 | 70d |
aReaction conditions: 20 mmol of amine substrate, 24 mmol of CS2, 40 mmol of K2CO3, room temperature. HPLC monitored the conversion. After the amine was totally consumed, the mixture was cooled to 0 °C, and 10 mmol of TCT in CH2Cl2 was added dropwise. The mixture was stirred for another 0.5 h and basified to pH >11 with 6 N NaOH. bThe reaction time for the first step. cIsolated yield. Data in the parenthesis is the isolated yield in 1-mol scale. d3.0 equiv of CS2 was used and the reaction temperature was 40 °C.