A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions

• Published in: Chemical science (Cambridge) Vol. 9; no. 20; pp. 4562 - 4568
• Main Authors: Shen, Xiang, Li, Yanjun, Wen, Zhaorui, Cao, Shi, Hou, Xinyi, Gong, Lei
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 2018
• Subjects: Carbonyl compounds; Carbonyls; Catalysis; Catalysts; Electron transfer
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c8sc01219a

The enantioselective photoredox reaction of α,β-unsaturated carbonyl compounds and tertiary/secondary α-silylamines was enabled by a readily available single Ni
-DBFOX catalyst (DBFOX = 4,6-bis((
)-4-phenyl-4,5-dihydrooxazol-2-yl)dibenzo[
,
]furan) under visible light conditions. The non-precious chiral catalyst is involved in the photochemical process to initiate single electron transfer and at the same time provides a well-organized chiral environment for the subsequent radical transformations. Good to excellent enantioselectivities (80-99% ee) were obtained for the formation of chiral γ-amino carboxylic acid derivatives and γ-lactams.