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ACS Catalysis
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Denard, C. A.; Huang, H.; Bartlett, M. J.; Lu, L.; Tan, Y.; Zhao, H.; Hartwig, J. F. Angew
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See the Supplementary Information for details of the point mutations that comprise these
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The yield obtained in the tandem reactions is significantly higher than the theoretical
yield from separate metathesis (37%) and epoxidation (34%) reactions. We hypothesize
that this is a result of the low aqueous solubility of Eꢀβꢀmethylstyrene (ca. 0.11 mg/mL),
which means that the epoxidation of 27 ꢁmol (3.19 mg Eꢀ3a) and 10 ꢁmol (37% of 27
ꢁmol) of Eꢀ3a have the same amount of substrate available for epoxidation at a given
time. This is also reflected in the higher yield obtained with KT32 on a smaller scale
(Table 3, Entry 6). However, in general it was found that the minimum substrate loading
required to obtain reliable and reproducible metathesis reactions was 0.027–0.054 mmol.
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