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. 2022 Mar 15;12(13):8263–8273. doi: 10.1039/d2ra00084a

Optimization of the reaction conditionsa.

graphic file with name d2ra00084a-u1.jpg
Entry Acid Solvent Yieldsb (%)
2a 3a
1 TMSOTf DCM 50 44
2 TMSOTf Toluene 48 43
3 TMSOTf THF 56 33
4 TMSOTf MeCN 44 <5
5 AgOTf DCM 44 17
6c (CuOTf)2·toluene DCM N.R. N.R.
7 Cu(OTf)2 DCM 58 15
8 Sc(OTf)3 DCM 52 24
9 Bi(OTf)3 DCM 47 30
10 Fe(OTf)3 DCM 52 30
11 In(OTf)3 DCM 62 20
12 Ac2O DCM N.R. N.R.
13 AlCl3 DCM 23 __d
14 BF3·OEt2 DCM 31 20
15 AcOH DCM 52 20
16 TfOH DCM 50 23
17c p-TsOH DCM N.R. N.R.
a

Reaction conditions: 1a (1.0 mmol), HMDS (0.5 mL, 2.4 mmol), acid (0.5 mmol), solvent (2 mL), MW (150 °C), 0.5 h.

b

Isolated yields.

c

No reaction occurred.

d

Unknown products were obtained.