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

Scope of DDQ/TBN-catalyzed aerobic allylation of isochromans 6a.

graphic file with name d4ra07586b-u4.jpg
Entry Product Yield (%)
8b 8′
1 graphic file with name d4ra07586b-u5.jpg 8b 76 8
2 graphic file with name d4ra07586b-u6.jpg 8c 80 (2.2 : 1)c 7
3 graphic file with name d4ra07586b-u7.jpg 8d 72 (2.9 : 1)c 10
4 graphic file with name d4ra07586b-u8.jpg 8e 50 (75) 14
5 graphic file with name d4ra07586b-u9.jpg 8f 66 (90)
6 graphic file with name d4ra07586b-u10.jpg 8g 48 42
7 graphic file with name d4ra07586b-u11.jpg 8h 18 (30)
8 graphic file with name d4ra07586b-u12.jpg 8i 33 (54)
9 graphic file with name d4ra07586b-u13.jpg 8j 34 (49)
10 graphic file with name d4ra07586b-u14.jpg 8k 41 (59)
11 graphic file with name d4ra07586b-u15.jpg 8l 37 (52)
12 graphic file with name d4ra07586b-u16.jpg 8m 12 (22)
13 graphic file with name d4ra07586b-u17.jpg 8n NRd
14 graphic file with name d4ra07586b-u18.jpg 8o NRd
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. Yields in the parentheses are based upon recovered starting material.

c

Only the diastereomeric ratio was obtained by the analysis of 1H NMR spectrum.

d

No reaction.