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. 2014 Mar 20;136(14):5287–5290. doi: 10.1021/ja502208z

Table 1. Metal-Catalyzed Synthesis of 2: Selected Optimizationa,b.

graphic file with name ja-2014-02208z_0004.jpg

entry conditions isolated yield (%)a
1 Fe2(ox)3·6H2O (5 equiv), NaBH4 (6.4 equiv), EtOH/H2O, 0 °C 0
2 Fe∥(Pc), NaBH4 (3.0 equiv), EtOH, 0 °C 0
3 Fe(acac)3, PhSiH3 (2.5 equiv), EtOH, 0 °C → rt 0
4 Co(acac)2, PhSiH3 (2.5 equiv), DCM/i-PrOH, –10 °C → rt 6
5 Mn(dpm)3, PhSiH3 (2.5 equiv), DCM/i-PrOH, –10 °C 34
6 Mn(dpm)3, PhSiH3 (2.5 equiv), DCM/i-PrOH, –10 °C 41b
7 Mn(dpm)3, PhSiH3 (2.5 equiv), t-BuOOH (1.5 equiv), DCM/i-PrOH, –10 °C 52b
a

Reaction performed on a 0.1 mmol scale using 20 mol % of metal catalyst unless otherwise stated.

b

Phenylsilane added slowly over 12 h as a solution in DCM. Pc = Phthalocyanine. ox = oxalate, acac = acetylacetonate.