C=CCCCCCC.CC(C1C=CC=CC=1)=C.C1=CCCCCCC1.C12CC(CC1)C=C2.CC1CC[C@@H](C(C)=C)CC=1.[CH3:43][C@H:44]1[C:49](=[O:50])[CH2:48][C@H:47]([C:51]([CH3:53])=[CH2:52])[CH2:46][CH2:45]1>>[CH:51]([CH:47]1[CH2:48][C:49](=[O:50])[CH:44]([CH3:43])[CH2:45][CH2:46]1)([CH3:53])[CH3:52]The yields of the hydrogenated products were determined by gas chromatography (GC). Hydrogenation of terminal alkenes such as 1-octene and α-methylstyrene proceeded readily within 24 hours at room temperature with excellent yields (see Table 1, entries 5-7). Internal alkenes trans-2-octene, cis-cyclooctene, and norbornylene were also hydrogenated at room temperature (see Table 1, entries 8-10). Hydrogenation of (R)-(+)-limonene occurred selectively at the terminal position; the internal tri-substituted C═C bond was not hydrogenated (see Table 1, entry 11). At room temperature, hydrogenation of (+)-dihydrocarvone occurred only at the C═C bond, affording 5-isopropyl-2-methylcyclohexanone in 99% yield (see Table 1, entry 12).
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