Table 3.

Examples of CuH-Catalyzed Amide Dehydration^a

^aReaction conditions: amide (1.0 mmol), copper(II) acetate (0.02 equiv), 1,2-bis(dicyclohexylphosphino)ethane (0.022 equiv), dimethoxy(methyl)silane (3 equiv) in THF (1 mL) at RT for 12 h. Yield represents the average isolated yield of two or more replicates. The yield enclosed in parentheses indicates the isolated yield of a single run wherein polymethylhydrosiloxane (PMHS, 4 equiv) was used instead of dimethoxy(methyl)silane. See supporting information for additional details.

^bToluene (1 mL) was used instead of THF.

^cAt 50 °C instead of RT.

^d4 equiv silane was used.