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. 2024 Dec 7;89(24):18585–18601. doi: 10.1021/acs.joc.4c02520

Table 4. Allylic Oxidation of 12a#: Scope and Limitations.

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entry 12 R1 R2 R3 Product yield (%)
1 12aa H H H 13aa 56
2 12ab F H H 13ab 85
3 12ac Cl H H 13ac 47
4 12ad Br H H 13ad 43
5 12ae I H H 13ae 29a
6 12af OCH3 H H 13af 78a
7 12ag OH H H 13ag <5b
8 12ah CH3 H H 13ah n.d.c
9 12ai CO2Et H H 13ai 36
10 12ak CF3 H H 13ak 22
11 12al H F H 13al 33
12 12am H Cl H 13am 60
13 12an H Br H 14an 26
14 12ao H I H 13ao n.d.c
15 12ap H OCH3 H 13ap 24
16 12aq H CH3 H 13aq 37
17 12ar H CO2CH3 H 14ar 48
18 12at H H OCH3 13at 56
19 12au H H CO2CH3 14au 92
a

Unprotected phenols 14ae (16%) and 14af (ca. 10%) were isolated as byproducts.

b

Decomposition of starting material.

c

n.d.: not determined; oxidation products 13 were detected by NMR but could not be isolated in pure form due to inseparable byproducts.