Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis

Herein, we report the redox-neutral allylation of aldehydes with readily available electron-rich allyl (hetero-) arenes, β-alkyl styrenes and allyl-diarylamines. This process was enabled by the combination of photoredox and chromium catalysis, which allowed a range of homoallylic alcohols to be prepared with high levels of selectivity for the anti diastereomer. Mechanistic investigations support the formation of an allyl chromium intermediate from allylic C(sp3)–H bonds and thus significantly extends the scope of the venerable Nozaki–Hiyama–Kishi reaction.