The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis.O ver the past two decades or so,m any improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays.However,there lacks aprotocol that could be used to couple awide range of chiral amines and aryl halides,w ithout erosion of the enantiomeric excess (ee). Reported in this article is am ethod based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines,amino alcohols,and amino acid esters with aryl bromides,w ith no need for any external photosensitizer.T he method is effective for aw ide variety of coupling partners,i ncluding those bearing functional groups sensitive to bases and nucleophiles,t hus providing av iable alternative to accessing synthetically important chiral N-aryl amines,amino alcohols,and amino acids esters.Its viability is demonstrated by 92 examples with up to 99 %ee. Scheme 1. Metal catalyzed C-N coupling of aryl halides for the synthesis of chiral N-aryl amines and amino acid esters.