Scope of the visible light-mediated ATRA reaction through reductive (RQ) and oxidative (OQ) quenching of 1a,b.
Entry | Substrate | Route | Time/min | Product | Yieldc/(%) |
---|---|---|---|---|---|
1 | RQ | 10 | 91 | ||
OQ | 40 | 92 | |||
2 | RQ | 10 | 93 | ||
OQ | 40 | 93 | |||
3 | RQ | 60 | 43 | ||
OQ | 40 | 35 | |||
4 | RQ | 10 | 90 | ||
OQ | 40 | 94 | |||
5 | RQ | 40 | 76 | ||
OQ | 40 | 57 | |||
6 | RQ | 40 | 58 | ||
OQ | 80 | 74 | |||
7 | RQ | 15 | 22 (cis : trans 17 : 5) | ||
OQ | 40 | 32 (cis : trans 25 : 7) | |||
8 | RQ | 15 | 80 | ||
OQ | 40 | 91 | |||
9 | RQ | 20 | 62 (E : Z 42 : 20) | ||
OQ | 80 | 81 (E : Z 65 : 16) | |||
10 | RQ | 10 | 93 | ||
OQ | 40 | 89 | |||
11 | RQ | 30 | 43 | ||
OQ | 40 | 87 | |||
RQ | 30 | 26 | |||
12 | RQ | 15 | 98 | ||
OQ | 40 | 97 | |||
13 | RQ | 30 | 63 | ||
14d | RQ | 45 | 49 | ||
OQ | 40 | 31 | |||
15 | RQ | 150 | 51 (E : Z 25 : 26) | ||
OQ | 150 | 49 (E : Z 25 : 24) |
Reaction conditions: RQ: 0.5 mol% (1), TEA (0.34 equiv.), (1.33 equiv.), 4 : 3 MeCN : MeOH.
Reaction conditions: OQ: 1.5 mol% (1), (1.33 equiv.), MeCN.
Isolated yield (%) after purification via silica gel column chromatography.
Intramolecular reaction. No external halide source was added.