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. Author manuscript; available in PMC: 2019 Jun 28.
Published in final edited form as: Tetrahedron. 2018 Mar 26;74(26):3358–3369. doi: 10.1016/j.tet.2018.03.045

Table 2.

Optimization of the tandem peroxidation reaction.

graphic file with name nihms956896u3.jpg
Entries/Conditionsa Yield %
1 Fe2(ox)3·6H2O (5.0 equiv), NaBH4 (6.4 equiv), EtOH/H2O, 0 °C 0
2 FeII(Pc), NaBH4 (3.0 equiv), EtOH, 0 °C 0
3 Fe(acac)3, PhSiH3 (2.5 equiv), EtOH, 0 °C to rt 0
4 Co(acac)2, PhSiH3 (2.5 equiv), DCM/i-PrOH, −10 °C to 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

PhSiH3 added slowly over 12 h as a solution in DCM. Pc = Phthalocyanine, ox = oxalate, acac = acetylacetonate, dpm = dipivaloylmethanato.

b