Fig. 4: Exploration of substrate scope for the synthesis of ketones from amides.
From: Chemodivergent transformations of amides using gem-diborylalkanes as pro-nucleophiles
Reaction condition A for primary amide: 1 (0.50 mmol), primiary amide P (0.25 mmol), nBuLi (1.0 mmol), THF (2.0 mL), 0 °C, 5 min then 100 °C for 12 h; Reaction condition B for secondary amide: 1 (0.50 mmol), secondary amide S (0.25 mmol), nBuLi (0.75 mmol), Al(OEt)3 (0.375 mmol), THF (2.0 mL), 0 °C, 5 min then 100 °C for 4 h. Reaction condition C for tertiary amide: 1 (0.375 mmol), tertiary amide T (0.25 mmol), MeLi (0.375 mmol), anisole (2.0 mL), 0 °C, 5 min then 120 °C for 2 h. For detailed conditions of trapping electrophiles, see Supplementary Information. Yields based on isolated products. a24 h. b12 h. cTHF was used instead of anisole. d1 (0.75 mmol), MeLi (0.75 mmol). eMeLi (0.625 mmol). f 8.0 mmol scale. Ad: adamantyl.
