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The transition-metal-catalyzed α-arylation of secondary amides remains a synthetic challenge due to the presence of a free N-H bond. We report a strategy to synthesize secondary α-aryl amides via a… Click to show full abstract
The transition-metal-catalyzed α-arylation of secondary amides remains a synthetic challenge due to the presence of a free N-H bond. We report a strategy to synthesize secondary α-aryl amides via a Ni-catalyzed reductive arylation of redox-active N-hydroxyphthalimide (NHP) esters of malonic acid half amides. This transformation proceeds under mild conditions and displays excellent chemoselectivity for amide α-arylation in the presence of other enolizable carbonyls. The NHP ester substrates are readily prepared from Meldrum's acid.
Journal Title: Organic letters
Year Published: 2022
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