Table 1 Reaction development.

Reaction conditions: 1a (0.2 mmol), DMTT (0.2 mmol), and base (0.4 mmol) in 2 ml of MeCN for 12 hours.


Embedded Image
EntryVariation from
the standard conditions
1b/1c/1d/1e*
1None90 (99% D)
†/0/0/0
2Without K2CO30/0/0/0
3Using KOH35 (99% D)/0/0/0
4Using DBU50 (99% D)/16/0/0
51.5 equiv of DMTT62 (99% D)/20/0/0
6CD3I (1.0 equiv.) instead of DMTT2/0/0/8
7CD3I (5.0 equiv) instead of DMTT7/0/43/10
8(CD3)2SO4 (1.0 equiv) instead of
DMTT
31/27/0/0
9DMSO-d6 instead of DMTT0/0/0/0
10[CD3Ph2S]+OTf instead of DMTT64/0/0/0

*1H NMR yields were presented using CH2Br2 as an internal standard.

†Isolated yield.

‡At 80°C.