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

DDQ/TBN-catalyzed aerobic allylation of other cyclic or acyclic ethers 6a.

graphic file with name d4ra07586b-u19.jpg
Entry Substrate Product Yield (%)
8b 8′ (lactone)
1 graphic file with name d4ra07586b-u20.jpg graphic file with name d4ra07586b-u21.jpg 86 8
2 graphic file with name d4ra07586b-u22.jpg graphic file with name d4ra07586b-u23.jpg 49 (62) 21
3 graphic file with name d4ra07586b-u24.jpg graphic file with name d4ra07586b-u25.jpg 31 (77) 17
4 graphic file with name d4ra07586b-u26.jpg graphic file with name d4ra07586b-u27.jpg 29
5 graphic file with name d4ra07586b-u28.jpg graphic file with name d4ra07586b-u29.jpg 30 (33)
6 graphic file with name d4ra07586b-u30.jpg graphic file with name d4ra07586b-u31.jpg NRc
a

Reaction conditions: (i) 6 (0.37 mmol), DDQ (0.074 mmol), TBN (0.074 mmol), O2, DCE (3.7 mL), 0 °C or rt, 36 h; (ii) allyltributyl stannane (0.75 mmol), LiPF6 (0.19 mmol), MSA (0.075 mmol), 80 °C, 24 h.

b

Isolated yield.

c

No reaction.