Visible-light induced cross-electrophile coupling of imines and anhydrides to synthesize alpha-amino ketones

alpha-Amino ketones are important motifs in synthetic and medicinal chemistry. Efficient methods to directly access these motifs from feasible precursors are, however, limited. Herein, a visible-light mediated reductive cross-electrophile coupling of readily available imines and anhydrides was developed. Under mild reaction conditions, the umpolung reactivity of diverse imines engaged with anhydrides gives a variety of alpha-amino ketones with good yields and a broad functional group compatibility. Primary mechanistic studies revealed that this transformation might proceed through a radical-radical cross coupling pathway dominantly.

Automated summary

alpha-amino ketones are important compounds in synthetic and medicinal chemistry. However, there are limited methods to directly access these compounds from available starting materials. This study developed a visible-light mediated reductive cross-electrophile coupling to synthesize alpha-amino ketones from easily accessible imines and anhydrides. Under mild reaction conditions, diverse imines reacted with anhydrides to give a variety of alpha-amino ketones with good yields and broad functional group compatibility. Primary mechanistic studies suggested that this transformation mainly proceeded through a radical-radical cross coupling pathway.