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. 2022 Jul 20;13(32):9165–9175. doi: 10.1039/d2sc02122f

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 graphic file with name d2sc02122f-u1.jpg RQ 10 graphic file with name d2sc02122f-u2.jpg 91
OQ 40 92
2 RQ 10 graphic file with name d2sc02122f-u3.jpg 93
OQ 40 93
3 RQ 60 graphic file with name d2sc02122f-u4.jpg 43
OQ 40 35
4 graphic file with name d2sc02122f-u5.jpg RQ 10 graphic file with name d2sc02122f-u6.jpg 90
OQ 40 94
5 graphic file with name d2sc02122f-u7.jpg RQ 40 graphic file with name d2sc02122f-u8.jpg 76
OQ 40 57
6 graphic file with name d2sc02122f-u9.jpg RQ 40 graphic file with name d2sc02122f-u10.jpg 58
OQ 80 74
7 graphic file with name d2sc02122f-u11.jpg RQ 15 graphic file with name d2sc02122f-u12.jpg 22 (cis : trans 17 : 5)
OQ 40 32 (cis : trans 25 : 7)
8 graphic file with name d2sc02122f-u13.jpg RQ 15 graphic file with name d2sc02122f-u14.jpg 80
OQ 40 91
9 graphic file with name d2sc02122f-u15.jpg RQ 20 graphic file with name d2sc02122f-u16.jpg 62 (E : Z 42 : 20)
OQ 80 81 (E : Z 65 : 16)
10 graphic file with name d2sc02122f-u17.jpg RQ 10 graphic file with name d2sc02122f-u18.jpg 93
OQ 40 89
11 graphic file with name d2sc02122f-u19.jpg RQ 30 graphic file with name d2sc02122f-u20.jpg 43
OQ 40 87
RQ 30 graphic file with name d2sc02122f-u21.jpg 26
12 graphic file with name d2sc02122f-u22.jpg RQ 15 graphic file with name d2sc02122f-u23.jpg 98
OQ 40 97
13 graphic file with name d2sc02122f-u24.jpg RQ 30 graphic file with name d2sc02122f-u25.jpg 63
14d graphic file with name d2sc02122f-u26.jpg RQ 45 graphic file with name d2sc02122f-u27.jpg 49
OQ 40 31
15 graphic file with name d2sc02122f-u28.jpg RQ 150 graphic file with name d2sc02122f-u29.jpg 51 (E : Z 25 : 26)
OQ 150 49 (E : Z 25 : 24)
a

Reaction conditions: RQ: 0.5 mol% (1), TEA (0.34 equiv.), Inline graphic (1.33 equiv.), 4 : 3 MeCN : MeOH.

b

Reaction conditions: OQ: 1.5 mol% (1), Inline graphic (1.33 equiv.), MeCN.

c

Isolated yield (%) after purification via silica gel column chromatography.

d

Intramolecular reaction. No external halide source was added.