Skip to main content
. 2024 Dec 17;14(53):39645–39652. doi: 10.1039/d4ra07586b

Initial screening of reactions conditions in the presence of a stoichiometric amount of DDQa.

graphic file with name d4ra07586b-u1.jpg
Entry Method Acid Solvent Temp (°C) Yieldb (%)
1 A CH3CN 25 NRe
2 A DCE 25 7
3c A DCE 25 11
4 A DCE 80 18
5 B TFA DCE 25 10
6 B TFA DCE 80 28
7 B MSA DCE 80 59
8d B CBSA DCE 80 58
graphic file with name d4ra07586b-u2.jpg
a

Reaction conditions: (Method A) (i) 6a (0.15 mmol), DDQ (0.22 mmol), MS 4 Å (20 mg), solvent (0.1 M), rt, 0.5 h; (ii) allyltributyl stannane (0.22 mmol), 24 h. (Method B) (i) 6a (0.37 mmol), DDQ (0.37 mmol), H2O (0.41 mmol), DCE (0.1 M), rt, 24 h; (ii) allyltributyl stannane (0.75 mmol), LiClO4 (0.37 mmol), acid (0.075 mmol), 24 h.

b

Isolated yield.

c

LiClO4 (0.5 equiv.) was added.

d

The reaction mixture was stirred for 6 h before allylstannane was added.

e

No reaction.