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. 2019 Feb 6;10(11):3408–3412. doi: 10.1039/c8sc05263h

Table 2. Optimising the use of unsymmetrical aminating agents a .

Inline graphic
Entry Reaction conditions Yield b (%)
6 7a
1 10 mol% AgOTf, CH2Cl2, –78 → +20 °C, 2 h 76 c
2 10 mol% AgOTf, THF, –78 → +20 °C, 2 h 85
3 (1) 10 mol% AgOTf, THF, –78 → +20 °C, 2 h 40 20
(2) KHMDS (2.0 equiv.), –78 → –40 °C, 2 h
4 (1) 10 mol% AgOTf, THF, –78 → +20 °C, 2 h 0 50
(2) KHMDS (3.0 equiv.), –78 → –40 °C, 3 h
5 (1) 10 mol% AgOTf, THF, –78 → +20 °C, 2 h 0 72
(2) KHMDS (3.0 equiv.), –78 → –20 °C, 2 h

aReactions performed using 0.36 mmol of 4a, 0.36 mmol of 2a in 3.6 ml solvent.

bIsolated yield.

cSimilar results obtained with 15 or 20 mol% catalyst.