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. 2024 Jul 9;146(29):19828–19838. doi: 10.1021/jacs.4c02682

Table 3. Control Experiments for the Vitamin B12-Catalyzed Addition/1,2-Phenyl Migrationa.

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entry deviation from the reaction conditions yield of3a[%]b
1 - 80
2 no B12 0
3 no Zn 0
4 no light 0
5 no B12, Zn and light 0
6 under air 7
7 no surfactant 31
8 no butan-1-ol 65
a

Optimized reaction conditions: diethyl 2-phenyl-2-vinylmalonate (1, 0.10 mmol), 1-bromododecane (3 equiv, 0.30 mmol), vitamin B12 (2.5 mol %), Zn (3 equiv), DTAC (0.35 mmol), n-BuOH (1.25 mmol), H2O (5 mL), green LEDs (525 nm), 16 h, 40 °C.

b

Yields determined by GC analysis with mesitylene as an internal standard.